Condensed cyclic compound, organic light-emitting device including the same, and display apparatus including the organic light-emitting device

ABSTRACT

A condensed cyclic compound is represented by Formula 1. An organic light-emitting device includes: a first electrode; a second electrode; and an organic layer between the first electrode and the second electrode and comprising an emission layer, the organic layer including the condensed cyclic compound represented by Formula 1. A display apparatus includes: a thin-film transistor comprising a source electrode, a drain electrode, and an active layer; and the organic light-emitting device.

CROSS-REFERENCE TO RELATED APPLICATION

This application claims priority to and the benefit of Korean PatentApplication No. 10-2018-0163316, filed on Dec. 17, 2018, in the KoreanIntellectual Property Office, the entire content of which isincorporated herein by reference.

BACKGROUND 1. Field

One or more embodiments of the present disclosure relate to a condensedcyclic compound, an organic light-emitting device including the same,and a display apparatus including the organic light-emitting device.

2. Description of the Related Art

Organic light-emitting devices are self-emission devices that have wideviewing angles, high contrast ratios, short response times, and thathave excellent characteristics in terms of brightness, driving voltage,and response speed, and produce full-color images.

An example of such an organic light-emitting device may include a firstelectrode on a substrate, and a hole transport region, an emissionlayer, an electron transport region, and a second electrode, which aresequentially on the first electrode. Holes provided from the firstelectrode may move toward the emission layer through the hole transportregion, and electrons provided from the second electrode may move towardthe emission layer through the electron transport region. Carriers, suchas holes and electrons, recombine in the emission layer to produceexcitons. These excitons transit (e.g., transition or relax) from anexcited state to a ground state, thereby generating light.

SUMMARY

One or more embodiments include a condensed cyclic compound, an organiclight-emitting device including the same, and a display apparatusincluding the organic light-emitting device.

Additional aspects of embodiments will be set forth in part in thedescription which follows and, in part, will be apparent from thedescription, or may be learned by practice of the presented embodiments.

An aspect of an embodiment of the present disclosure provides acondensed cyclic compound represented by Formula 1:

(A₁₁)_(n11)-(L₁₁)_(a11)-(A₁₂)_(n12).   Formula 1

In Formula 1,

L₁₁ may be selected from a substituted or unsubstituted C₅-C₆₀carbocyclic group and a substituted or unsubstituted C₁-C₆₀ heterocyclicgroup,

a11 may be an integer of 0 to 5,

A₁₁ and A₁₂ may each independently be selected from a group representedby Formula 1A and a group represented by Formula 1B, and

n11 and n12 may each independently be an integer from 1 to 3:

In Formulae 1A and 1B,

X₁₁ may be selected from C(R₁₄)(R₁₅), Si(R₁₄)(R₁₅), O, and S,

X₁₂ may be selected from C(R₁₆)(R₁₇), Si(R₁₆)(R₁₇), O, and S,

R₁₁ to R₁₇ may each independently be selected from hydrogen, deuterium,—F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, asubstituted or unsubstituted C₁-C₆₀ alkyl group, a substituted orunsubstituted C₂-C₆₀ alkenyl group, a substituted or unsubstitutedC₂-C₆₀ alkynyl group, a substituted or unsubstituted C₁-C₆₀ alkoxygroup, a substituted or unsubstituted C₃-C₁₀ cycloalkyl group, asubstituted or unsubstituted C₁-C₁₀ heterocycloalkyl group, asubstituted or unsubstituted C₃-C₁₀ cycloalkenyl group, a substituted orunsubstituted C₁-C₁₀ heterocycloalkenyl group, a substituted orunsubstituted C₆-C₆₀ aryl group, a substituted or unsubstituted C₆-C₆₀aryloxy group, a substituted or unsubstituted C₆-C₆₀ arylthio group, asubstituted or unsubstituted C₁-C₆₀ heteroaryl group, a substituted orunsubstituted C₁-C₆₀ heteroaryloxy group, a substituted or unsubstitutedC₁-C₆₀ heteroarylthio group, a substituted or unsubstituted monovalentnon-aromatic condensed polycyclic group, a substituted or unsubstitutedmonovalent non-aromatic condensed heteropolycyclic group,—Si(Q₁)(Q₂)(Q₃), —B(Q₁)(Q₂), —N(Q₁)(Q₂), —P(Q₁)(Q₂), —C(═O)(Q₁),—S(═O)(Q₁), —S(═O)₂(Q₁), —P(═O)(Q₁)(Q₂), and —P(═S)(Q₁)(Q₂),

b11 may be selected from 1 and 2,

b12 and b13 may each independently be an integer from 1 to 3,

Q₁ to Q₃ may each independently be selected from hydrogen, deuterium,—F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, aC₁-C₆₀ alkyl group, a C₂-C₆₀ alkenyl group, a C₂-C₆₀ alkynyl group, aC₁-C₆₀ alkoxy group, a C₃-C₁₀ cycloalkyl group, a C₁-C₁₀heterocycloalkyl group, a C₃-C₁₀ cycloalkenyl group, a C₁-C₁₀heterocycloalkenyl group, a C₆-C₆₀ aryl group, a C₆-C₆₀ aryloxy group, aC₆-C₆₀ arylthio group, a C₁-C₆₀ heteroaryl group, a C₁-C₆₀ heteroaryloxygroup, a C₁-C₆₀ heteroarylthio group, a monovalent non-aromaticcondensed polycyclic group, a monovalent non-aromatic condensedheteropolycyclic group, a biphenyl group, and a terphenyl group, and

* indicates a binding site to a neighboring atom.

Another aspect of an embodiment of the present disclosure provides anorganic light-emitting device including: a first electrode; a secondelectrode; and an organic layer between the first electrode and thesecond electrode and including an emission layer, wherein the organiclayer includes the condensed cyclic compound described above.

Another aspect of an embodiment of the present disclosure provides adisplay apparatus including: a thin-film transistor including a sourceelectrode, a drain electrode, and an active layer; and the organiclight-emitting device described above, wherein the first electrode ofthe organic light-emitting device is electrically coupled to oneselected from the source electrode and the drain electrode of thethin-film transistor.

BRIEF DESCRIPTION OF THE DRAWINGS

These and/or other aspects of embodiments will become apparent and morereadily appreciated from the following description of the embodiments,taken in conjunction with the accompanying drawings in which:

FIG. 1 is a schematic cross-sectional view of an organic light-emittingdevice according to an embodiment;

FIG. 2 is a schematic cross-sectional view of an organic light-emittingdevice according to an embodiment;

FIG. 3 is a schematic cross-sectional view of an organic light-emittingdevice according to an embodiment; and

FIG. 4 is a schematic cross-sectional view of an organic light-emittingdevice according to an embodiment.

DETAILED DESCRIPTION

The subject matter of the present disclosure will now be described morefully with reference to exemplary embodiments. The subject matter of thedisclosure may, however, be embodied in many different forms and shouldnot be construed as being limited to the embodiments set forth herein;rather, these embodiments are provided so that this disclosure will bethorough and complete, and will fully convey the subject matter of thedisclosure to those skilled in the art. Features of embodiments of thepresent disclosure, and how to achieve them, will become apparent byreference to the embodiments that will be described herein below in moredetail, together with the accompanying drawings. The subject matter ofthe present disclosure may, however, be embodied in many different formsand should not be limited to the exemplary embodiments.

Hereinafter, embodiments are described in more detail by referring tothe accompanying drawings, and in the drawings, like reference numeralsdenote like elements, and a redundant explanation thereof will not berepeated herein.

As used herein, the singular forms “a,” “an” and “the” are intended toinclude the plural forms as well, unless the context clearly indicatesotherwise.

It will be further understood that the terms “comprises” and/or“comprising,” as used herein, specify the presence of stated features orcomponents, but do not preclude the presence or addition of one or moreother features or components. As used herein, the term “and/or” includesany and all combinations of one or more of the associated listed items.Expressions such as “at least one of,” when preceding a list ofelements, modify the entire list of elements and do not modify theindividual elements of the list.

It will be understood that when a layer, region, or component isreferred to as being “on” or “onto” another layer, region, or component,it may be directly or indirectly formed on the other layer, region, orcomponent. For example, intervening layers, regions, or components maybe present. In addition, it will also be understood that when an elementor layer is referred to as being “between” two elements or layers, itcan be the only element or layer between the two elements or layers, orone or more intervening elements or layers may also be present.

Sizes of components in the drawings may be exaggerated for convenienceof explanation. In other words, because sizes and thicknesses ofcomponents in the drawings may be arbitrarily illustrated forconvenience of explanation, the following embodiments of the presentdisclosure are not limited thereto.

The term “organic layer,” as used herein, refers to a single layerand/or a plurality of layers between the first electrode and the secondelectrode of the organic light-emitting device. A material included inthe “organic layer” is not limited to an organic material. For example,the organic layer may include an inorganic material.

A condensed cyclic compound according to an embodiment is represented byFormula 1:

(A₁₁)_(n11)-(L₁₁)_(a11)-(A₁₂)_(n12)   Formula 1

In Formula 1, L₁₁ may be selected from a substituted or unsubstitutedC₅-C₆₀ carbocyclic group and a substituted or unsubstituted C₁-C₆₀heterocyclic group.

For example, in Formula 1, L₁₁ may be selected from:

a C₅-C₆₀ carbocyclic group; and

a C₅-C₆₀ carbocyclic group substituted with at least one selected fromdeuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitrogroup, a C₁-C₂₀ alkyl group, a C₁-C₂₀ alkoxy group, a C₆-C₃₀ aryl group,and a monovalent non-aromatic condensed polycyclic group, and

Q₃₁ to Q₃₃ may each independently be selected from a C₁-C₂₀ alkyl groupand a C₆-C₃₀ aryl group, but embodiments of the present disclosure arenot limited thereto.

In one embodiment, in Formula 1, L₁₁ may be selected from:

a benzene group, a naphthalene group, a fluorene group, aspiro-bifluorene group, a benzofluorene group, a dibenzofluorene group,a phenanthrene group, an anthracene group, a fluoranthene group, atriphenylene group, a pyrene group, a chrysene group, and a perylenegroup; and

a benzene group, a naphthalene group, a fluorene group, aspiro-bifluorene group, a benzofluorene group, a dibenzofluorene group,a phenanthrene group, an anthracene group, a fluoranthene group, atriphenylene group, a pyrene group, a chrysene group, and a perylenegroup, each substituted with at least one selected from deuterium, —F,—Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, a C₁-C₂₀alkyl group, a C₁-C₂₀ alkoxy group, a phenyl group, a biphenyl group, aterphenyl group, a naphthyl group, a fluorenyl group, aspiro-bifluorenyl group, a benzofluorenyl group, a dibenzofluorenylgroup, a phenanthrenyl group, an anthracenyl group, a fluoranthenylgroup, a triphenylenyl group, a pyrenyl group, a chrysenyl group, and aperylenyl group,

Q₃₁ to Q₃₃ may each independently be selected from a C₁-C₂₀ alkyl groupand a C₆-C₃₀ aryl group, but embodiments of the present disclosure arenot limited thereto.

In one embodiment, in Formula 1, L₁₁ may be selected from groupsrepresented by Formulae 4-1 to 4-35, but embodiments of the presentdisclosure are not limited thereto:

In Formulae 4-1 to 4-35,

X₄₁ may be C(R₄₃)(R₄₄),

R₄₁ to R₄₄ may each independently be selected from hydrogen, deuterium,—F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, aC₁-C₂₀ alkyl group, a C₁-C₂₀ alkoxy group, a phenyl group, a biphenylgroup, a terphenyl group, a naphthyl group, a fluorenyl group, aspiro-bifluorenyl group, a benzofluorenyl group, a dibenzofluorenylgroup, a phenanthrenyl group, an anthracenyl group, a fluoranthenylgroup, a triphenylenyl group, a pyrenyl group, a chrysenyl group, and aperylenyl group,

b41 may be selected from 1, 2, 3, and 4,

b42 may be selected from 1, 2, 3, 4, 5, and 6,

b43 may be selected from 1, 2, 3, 4, 5, 6, 7, and 8,

b44 may be selected from 1, 2, 3, 4, and 5,

b45 may be selected from 1, 2, and 3,

b46 may be selected from 1 and 2, and

* and *′ each indicate a binding site to a neighboring atom.

In one embodiment, in Formula 1, L₁₁ may be selected from groupsrepresented by Formulae 4-1 to 4-17, but embodiments of the presentdisclosure are not limited thereto.

In one embodiment, in Formula 1, L₁₁ may be selected from groupsrepresented by Formulae 4-1 to 4-12, but embodiments of the presentdisclosure are not limited thereto.

In Formula 1, a11 indicates the repeating number of L₁₁(s), and a11 maybe an integer from 0 to 5. When a11 is two or more, two or more L₁₁(s)may be identical to or different from each other.

For example, in Formula 1, a11 may be selected from 0, 1, and 2, butembodiments of the present disclosure are not limited thereto.

In Formula 1, A₁₁ and A₁₂ may each independently be selected from agroup represented by Formula 1A and a group represented by Formula 1B:

In Formulae 1A and 1B, X₁₁, X₁₂, R₁₁ to R₁₃, and b11 to b13 may eachindependently be the same as described herein below, and * indicates abinding site to a neighboring atom.

In Formulae 1A and 1B, X₁₁ may be selected from C(R₁₄)(R₁₅),Si(R₁₄)(R₁₅), O, and S.

For example, in Formulae 1A and 1B, X₁₁ may be C(R₁₄)(R₁₅), butembodiments of the present disclosure are not limited thereto.

In Formulae 1A and 1B, X₁₂ may be selected from C(R₁₆)(R₁₇),Si(R₁₆)(R₁₇), O, and S.

In Formulae 1A and 1B, X₁₂ may be C(R₁₆)(R₁₇), but embodiments of thepresent disclosure are not limited thereto.

In Formulae 1A and 1B, R₁₁ to R₁₇ may each independently be selectedfrom hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyanogroup, a nitro group, a substituted or unsubstituted C₁-C₆₀ alkyl group,a substituted or unsubstituted C₂-C₆₀ alkenyl group, a substituted orunsubstituted C₂-C₆₀ alkynyl group, a substituted or unsubstitutedC₁-C₆₀ alkoxy group, a substituted or unsubstituted C₃-C₁₀ cycloalkylgroup, a substituted or unsubstituted C₁-C₁₀ heterocycloalkyl group, asubstituted or unsubstituted C₃-C₁₀ cycloalkenyl group, a substituted orunsubstituted C₁-C₁₀ heterocycloalkenyl group, a substituted orunsubstituted C₆-C₆₀ aryl group, a substituted or unsubstituted C₆-C₆₀aryloxy group, a substituted or unsubstituted C₆-C₆₀ arylthio group, asubstituted or unsubstituted C₁-C₆₀ heteroaryl group, a substituted orunsubstituted C₁-C₆₀ heteroaryloxy group, a substituted or unsubstitutedC₁-C₆₀ heteroarylthio group, a substituted or unsubstituted monovalentnon-aromatic condensed polycyclic group, a substituted or unsubstitutedmonovalent non-aromatic condensed heteropolycyclic group,—Si(Q₁)(Q₂)(Q₃), —B(Q₁)(Q₂), —N(Q₁)(Q₂), —P(Q₁)(Q₂), —C(═O)(Q₁),—S(═O)(Q₁), —S(═O)₂(Q₁), —P(═O)(Q₁)(Q₂), and —P(═S)(Q₁)(Q₂), and

Q₁ to Q₃ may each independently be selected from hydrogen, deuterium,—F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, aC₁-C₆₀ alkyl group, a C₂-C₆₀ alkenyl group, a C₂-C₆₀ alkynyl group, aC₁-C₆₀ alkoxy group, a C₃-C₁₀ cycloalkyl group, a C₁-C₁₀heterocycloalkyl group, a C₃-C₁₀ cycloalkenyl group, a C₁-C₁₀heterocycloalkenyl group, a C₆-C₆₀ aryl group, a C₆-C₆₀ aryloxy group, aC₆-C₆₀ arylthio group, a C₁-C₆₀ heteroaryl group, a C₁-C₆₀ heteroaryloxygroup, a C₁-C₆₀ heteroarylthio group, a monovalent non-aromaticcondensed polycyclic group, a monovalent non-aromatic condensedheteropolycyclic group, a biphenyl group, and a terphenyl group.

For example, in Formulae 1A and 1B, R₁₁ to R₁₇ may each independently beselected from:

hydrogen, deuterium, —F, —Cl, —Br, —I, a cyano group, a C₁-C₂₀ alkylgroup, and a C₁-C₂₀ alkoxy group;

a C₁-C₂₀ alkyl group and a C₁-C₂₀ alkoxy group, each substituted with atleast one selected from deuterium, —F, —Cl, —Br, —I, a cyano group, aphenyl group, a biphenyl group, and a terphenyl group;

a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, acyclopentenyl group, a cyclohexenyl group, a phenyl group, a biphenylgroup, a terphenyl group, a pentalenyl group, an indenyl group, anaphthyl group, an azulenyl group, an indacenyl group, an acenaphthylgroup, a fluorenyl group, a spiro-bifluorenyl group, a benzofluorenylgroup, a dibenzofluorenyl group, a phenalenyl group, a phenanthrenylgroup, an anthracenyl group, a fluoranthenyl group, a triphenylenylgroup, a pyrenyl group, a chrysenyl group, a perylenyl group, and apentacenyl group; and

a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, acyclopentenyl group, a cyclohexenyl group, a phenyl group, a biphenylgroup, a terphenyl group, a pentalenyl group, an indenyl group, anaphthyl group, an azulenyl group, an indacenyl group, an acenaphthylgroup, a fluorenyl group, a spiro-bifluorenyl group, a benzofluorenylgroup, a dibenzofluorenyl group, a phenalenyl group, a phenanthrenylgroup, an anthracenyl group, a fluoranthenyl group, a triphenylenylgroup, a pyrenyl group, a chrysenyl group, a perylenyl group, and apentacenyl group, each substituted with at least one selected fromdeuterium, —F, —Cl, —Br, —I, a cyano group, a C₁-C₂₀ alkyl group, aC₁-C₂₀ alkoxy group, a cyclopentyl group, a cyclohexyl group, acycloheptyl group, a cyclopentenyl group, a cyclohexenyl group, a phenylgroup, a biphenyl group, a terphenyl group, a pentalenyl group, anindenyl group, a naphthyl group, an azulenyl group, an indacenyl group,an acenaphthyl group, a fluorenyl group, a spiro-bifluorenyl group, abenzofluorenyl group, a dibenzofluorenyl group, a phenalenyl group, aphenanthrenyl group, an anthracenyl group, a fluoranthenyl group, atriphenylenyl group, a pyrenyl group, a chrysenyl group, a perylenylgroup, and a pentacenyl group, but embodiments of the present disclosureare not limited thereto.

In one embodiment, in Formulae 1A and 1B, R₁₁ to R₁₇ may eachindependently be selected from:

hydrogen, deuterium, —F, —Cl, —Br, —I, a cyano group, a C₁-C₂₀ alkylgroup;

a C₁-C₂₀ alkyl group substituted with at least one selected fromdeuterium, —F, —Cl, —Br, —I, and a cyano group; and

groups represented by Formulae 5-1 to 5-9, but embodiments of thepresent disclosure are not limited thereto:

In Formulae 5-1 to 5-9,

R₅₁ and R₅₂ may each independently be selected from hydrogen, deuterium,—F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, aC₁-C₂₀ alkyl group, a C₁-C₂₀ alkoxy group, a phenyl group, a biphenylgroup, a terphenyl group, a naphthyl group, a fluorenyl group, aspiro-bifluorenyl group, a benzofluorenyl group, a dibenzofluorenylgroup, a phenanthrenyl group, an anthracenyl group, a fluoranthenylgroup, a triphenylenyl group, a pyrenyl group, a chrysenyl group, and aperylenyl group,

b51 may be selected from 1, 2, 3, 4, and 5,

b52 may be selected from 1, 2, 3, 4, 5, 6, and 7,

b53 may be selected from 1, 2, 3, 4, 5, 6, 7, 8, and 9,

b54 may be selected from 1, 2, 3, and 4, and

* indicates a binding site to a neighboring atom.

In one embodiment, in Formulae 1A and 1B, R₁₁ to R₁₇ may eachindependently be selected from:

hydrogen, deuterium, —F, —Cl, —Br, —I, a cyano group, a methyl group, anethyl group, an n-propyl group, an isopropyl group, an n-butyl group, anisobutyl group, a sec-butyl group, and a tert-butyl group;

a methyl group, an ethyl group, an n-propyl group, an isopropyl group,an n-butyl group, an isobutyl group, a sec-butyl group, and a tert-butylgroup, each substituted with at least one selected from deuterium, —F,—Cl, —Br, —I, and a cyano group; and

groups represented by Formulae 6-1 to 6-74, but embodiments of thepresent disclosure are not limited thereto:

In Formulae 6-1 to 6-74,

i-Pr indicates an isopropyl group,

t-Bu indicates a tert-butyl group,

Ph indicates a phenyl group,

1-Naph indicates a 1-naphthyl group,

2-Naph indicates a 2-naphthyl group, and

* indicates a binding site to a neighboring atom.

In Formulae 1A and 1B, b11 may be selected from 1 and 2.

In Formulae 1A and 1B, b12 and b13 may each independently be an integerfrom 1 to 3.

In one embodiment, in Formula 1, A₁₁ and A₁₂ may each independently be agroup represented by Formula 1A, but embodiments of the presentdisclosure are not limited thereto.

In Formula 1, n11 indicates the substitution number of A₁₁(s), n12indicates the substitution number of A₁₂(s), and n11 and n12 may eachindependently be an integer from 1 to 3.

For example, in Formula 1, n11 and n12 may each independently beselected from 1 and 2, but embodiments of the present disclosure are notlimited thereto.

In one embodiment, in Formula 1, the sum of n11 and n12 may be selectedfrom 2 and 3, but embodiments of the present disclosure are not limitedthereto.

In one embodiment, in Formula 1, n11 and n12 may each independently be1, but embodiments of the present disclosure are not limited thereto.

In one embodiment, in Formula 1, L₁₁ may be selected from groupsrepresented by Formulae 4-1 to 4-12, and a11 may be selected from 0, 1,and 2, but embodiments of the present disclosure are not limitedthereto.

In one embodiment, the condensed cyclic compound may be represented byone selected from Formulae 1-1 and 1-2, but embodiments of the presentdisclosure are not limited thereto:

In Formulae 1-1 and 1-2,

L₁₁ and a11 may each independently be the same as defined in connectionwith Formula 1,

X_(11a) and X_(11b) may each independently be the same as defined inconnection with X₁₁ in Formula 1A,

X_(12a) and X_(12b) may each independently be the same as defined inconnection with X₁₂ in Formula 1A,

R_(11a), R_(11b), R_(12a), R_(12b), R_(13a), and R_(13b) may eachindependently be the same as defined in connection with R₁₁ in Formula1A,

b11a and b11b may each independently be the same as defined inconnection with b11 in Formula 1A, and

b12a, b12b, b13a, and b13b may each independently be the same as definedin connection with b12 in Formula 1A.

In one embodiment, the condensed cyclic compound may be represented byone selected from Formulae 1-11 and 1-12, but embodiments of the presentdisclosure are not limited thereto:

In Formulae 1-11 and 1-12,

L₁₁ may be selected from groups represented by Formulae 4-1 to 4-12;

In Formulae 4-1 to 4-12,

R₄₁ may be selected from hydrogen, deuterium, —F, —Cl, —Br, —I, ahydroxyl group, a cyano group, a nitro group, a C₁-C₂₀ alkyl group, aC₁-C₂₀ alkoxy group, a phenyl group, a biphenyl group, a terphenylgroup, a naphthyl group, a fluorenyl group, a spiro-bifluorenyl group, abenzofluorenyl group, a dibenzofluorenyl group, a phenanthrenyl group,an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, apyrenyl group, a chrysenyl group, and a perylenyl group,

b41 may be selected from 1, 2, 3, and 4,

b42 may be selected from 1, 2, 3, 4, 5, and 6,

* and *′ each indicate a binding site to a neighboring atom,

a11 may be selected from 0, 1, and 2,

R_(11a), R_(11b), R_(12a), R_(12b), R_(13a), R_(13b), R_(14a), R_(14b),R_(15a), R_(15b), R_(16a), R_(16b), R_(17a), and R_(17b) may eachindependently be the same as defined in connection with R₁₁ in Formula1A,

b11a and b11b may each independently be the same defined in connectionwith b11 in Formula 1A, and

b12a, b12b, b13a, and b13b may each independently be the same defined inconnection with b12 in Formula 1A.

In one embodiment, the condensed cyclic compound may be selected fromCompounds 1 to 6, but embodiments of the present disclosure are notlimited thereto:

In some embodiments, the condensed cyclic compound does not include anamine moiety and a carbazole moiety. For example, in some embodimentsthe condensed cyclic compound is free of an amine moiety and/or acarbazole moiety.

In general, an amine moiety or a carbazole moiety has high holetransport characteristics, but has a carbon-nitrogen single bond havingrelatively low bond dissociation energy (BDE). Therefore, molecularstability may be lower in compounds that include an amine moiety and/ora carbazole moiety. Because a compound including an amine moiety or acarbazole moiety receives electrons in an excited state and decomposes,a lifespan of an organic light-emitting device including the compoundmay be shortened or reduced.

On the other hand, because the condensed cyclic compound has relativelyhigh BDE, a lifespan of an organic light-emitting device including thecondensed cyclic compound may be improved. As used herein, the term“bond dissociation energy” or “BDE” refers to the amount of energyrequired for the homolytic breaking of a chemical bond (e.g., a covalentchemical bond). In embodiments of the disclosure, the “lowest bonddissociation energy” or “BDE” refers to the chemical bond of thecondensed cyclic compound having the lowest bond dissociation energy.For example, in some embodiments, the bond dissociation energy disclosedherein refers to the bond dissociation energy of a carbon-nitrogen bondof the condensed cyclic compound. In some embodiments, the bonddissociation energy disclosed herein refers to a carbon-nitrogen bond ofA₁₁, A₁₂, Formula 1A, or Formula 1B.

In some embodiments, the BDE of the condensed cyclic compound may exceed(e.g., be greater than) about 1.8 eV, for example, 3.0 eV or more, butembodiments of the present disclosure are not limited thereto. Forexample, the lowest BDE of the condensed cyclic compound is in a rangeof 1.8 eV to 10.0 eV, 3.0 eV to 10.0 eV, or, for example, 3.5 eV to 10.0eV. When the BDE of the condensed cyclic compound is within this range,an organic light-emitting device having a lifespan of an available levelmay be provided.

The condensed cyclic compound represented by Formula 1 may besynthesized by using any suitable organic synthetic method generallyused in the art. A synthesis method of the organometallic compound maybe recognizable by one of ordinary skill upon reviewing the followingdescription of example embodiments.

At least one of the condensed cyclic compound of Formula 1 may be usedbetween a pair of electrodes of an organic light-emitting device. Forexample, the condensed cyclic compound may be included in at least onelayer selected from a hole transport region, an electron transportregion, and an emission layer.

In one or more embodiments, the condensed cyclic compound of Formula 1may be used as a material for a capping layer located outside a pair ofelectrodes of an organic light-emitting device.

In one embodiment, the emission layer may include the condensed cycliccompound, but embodiments of the present disclosure are not limitedthereto. In one embodiment, the emission layer may further include aphosphorescent dopant or a delayed fluorescent dopant. In this case, thecondensed cyclic compound may act as a host.

In one embodiment, the first electrode may be an anode,

the second electrode may be a cathode,

the organic layer may further include a hole transport region betweenthe first electrode and the emission layer and/or an electron transportregion between the emission layer and the second electrode,

the hole transport region may include a hole injection layer, a holetransport layer, an emission auxiliary layer, an electron blockinglayer, or any combination thereof, and

the electron transport region may include a hole blocking layer, anelectron transport layer, an electron injection layer, or anycombination thereof.

For example, the electron blocking layer may include the condensedcyclic compound. In one embodiment, the emission layer may include ahost and may satisfy Condition 1, but embodiments of the presentdisclosure are not limited thereto:

BDE(C ⁻)>T ₁(H).   Condition 1

In Condition 1,

BDE(C⁻) is the bond dissociation energy in the case where the bond isdissociated by the excitation energy of the neighboring host when thecondensed cyclic compound is in an anion state, and

T₁(H) is the lowest excitation triplet energy level of the host.

On the other hand, the electron blocking layer may include the condensedcyclic compound, and the emission layer may include the host and satisfyCondition 2, but embodiments of the present disclosure are not limitedthereto:

HOMO (H)−HOMO (C)|≤0.3 eV.   Condition 2

In condition 2,

HOMO (H) is the highest occupied molecular orbital energy level of thehost, and

HOMO (C) is the highest occupied molecular orbital energy level of thecondensed cyclic compound.

Because the organic light-emitting device satisfying Condition 2 hasimproved hole injection characteristics from the electron blocking layerto the host, the lifespan of the organic light-emitting device may beimproved.

The expression “(an organic layer) includes at least one condensedcyclic compound,” as used herein, may include a case in which “(anorganic layer) includes identical compounds represented by Formula 1”and a case in which “(an organic layer) includes two or more differentcondensed cyclic compounds represented by Formula 1.”

For example, the organic layer may include, as the condensed cycliccompound, only Compound 1. In this regard, Compound 1 may be present inan emission layer of the organic light-emitting device. In one or moreembodiments, the organic layer may include, as the condensed cycliccompound, Compound 1 and Compound 2. In this regard, Compound 1 andCompound 2 may be present in an identical layer (for example, Compound 1and Compound 2 may all exist in an emission layer), or different layers(for example, Compound 1 may exist in an emission layer and Compound 2may exist in an electron transport layer).

The organic layer includes i) a hole transport region that is betweenthe first electrode (anode) and the emission layer and includes at leastone of a hole injection layer, a hole transport layer, a buffer layer,and an electron blocking layer, and ii) an electron transport regionthat is between the emission layer and the second electrode (cathode)and includes at least one selected from a hole blocking layer, anelectron transport layer, and an electron injection layer. The emissionlayer may include at least one of the condensed compound represented byFormula 1.

The term “organic layer,” as used herein, refers to a single layerand/or a plurality of layers between the first electrode and the secondelectrode of the organic light-emitting device. A material included inthe “organic layer” is not limited to an organic material. For example,the organic layer may include an inorganic material.

Description of FIG. 1

FIG. 1 is a schematic view of an organic light-emitting device 10according to an embodiment. The organic light-emitting device 10includes a first electrode 110, an organic layer 150, and a secondelectrode 190.

Hereinafter, the structure of the organic light-emitting device 10according to an embodiment and a method of manufacturing the organiclight-emitting device 10 will be described in connection with FIG. 1.

First Electrode 110

In FIG. 1, a substrate may be additionally located under the firstelectrode 110 or above the second electrode 190. The substrate may be aglass substrate or a plastic substrate, each having excellent mechanicalstrength, thermal stability, transparency, surface smoothness, ease ofhandling, and water resistance.

The first electrode 110 may be formed by depositing or sputtering amaterial for forming the first electrode 110 on the substrate. When thefirst electrode 110 is an anode, the material for a first electrode maybe selected from materials with a high work function to facilitate holeinjection.

The first electrode 110 may be a reflective electrode, asemi-transmissive electrode, or a transmissive electrode. When the firstelectrode 110 is a transmissive electrode, a material for forming afirst electrode may be selected from indium tin oxide (ITO), indium zincoxide (IZO), tin oxide (SnO₂), zinc oxide (ZnO), and any combinationsthereof, but embodiments of the present disclosure are not limitedthereto. In one or more embodiments, when the first electrode 110 is asemi-transmissive electrode or a reflective electrode, a material forforming a first electrode may be selected from magnesium (Mg), silver(Ag), aluminum (Al), aluminum-lithium (Al—Li), calcium (Ca),magnesium-indium (Mg—In), magnesium-silver (Mg—Ag), and any combinationsthereof, but embodiments of the present disclosure are not limitedthereto.

The first electrode 110 may have a single-layered structure, or amulti-layered structure including two or more layers. For example, thefirst electrode 110 may have a three-layered structure of ITO/Ag/ITO,but the structure of the first electrode 110 is not limited thereto.

Organic Layer 150

The organic layer 150 is on the first electrode 110. The organic layer150 may include an emission layer.

The organic layer 150 may further include a hole transport regionbetween the first electrode 110 and the emission layer, and/or anelectron transport region between the emission layer and the secondelectrode 190.

[Hole Transport Region in Organic Layer 150

The hole transport region may have i) a single-layered structureincluding a single layer including a single material, ii) asingle-layered structure including a single layer including a pluralityof different materials, or iii) a multi-layered structure having aplurality of layers including a plurality of different materials.

The hole transport region may include at least one layer selected from ahole injection layer, a hole transport layer, an emission auxiliarylayer, and an electron blocking layer.

For example, the hole transport region may have a single-layeredstructure including a single layer including a plurality of differentmaterials, or a multi-layered structure having a hole injectionlayer/hole transport layer structure, a hole injection layer/holetransport layer/emission auxiliary layer structure, a hole injectionlayer/emission auxiliary layer structure, a hole transportlayer/emission auxiliary layer structure, or a hole injection layer/holetransport layer/electron blocking layer structure, wherein for eachstructure, constituting layers are sequentially stacked from the firstelectrode 110 in this stated order, but the structure of the holetransport region is not limited thereto.

The hole transport region may include at least one selected fromm-MTDATA, TDATA, 2-TNATA, NPB(NPD), β-NPB, TPD, spiro-TPD, spiro-NPB,methylated-NPB, TAPC, HMTPD, 4,4′,4″-tris(N-carbazolyl)triphenylamine(TCTA), polyaniline/dodecylbenzenesulfonic acid (PANI/DBSA),poly(3,4-ethylenedioxythiophene)/poly(4-styrenesulfonate) (PEDOT/PSS),polyaniline/camphor sulfonic acid (PANI/CSA),polyaniline/poly(4-styrenesulfonate) (PANI/PSS), a compound representedby Formula 201, and a compound represented by Formula 202:

In Formulae 201 and 202,

L₂₀₁ to L₂₀₄ may each independently be selected from a substituted orunsubstituted C₃-C₁₀ cycloalkylene group, a substituted or unsubstitutedC₁-C₁₀ heterocycloalkylene group, a substituted or unsubstituted C₃-C₁₀cycloalkenylene group, a substituted or unsubstituted C₁-C₁₀heterocycloalkenylene group, a substituted or unsubstituted C₆-C₆₀arylene group, a substituted or unsubstituted C₁-C₆₀ heteroarylenegroup, a substituted or unsubstituted divalent non-aromatic condensedpolycyclic group, and a substituted or unsubstituted divalentnon-aromatic condensed heteropolycyclic group;

L₂₀₅ may be selected from *—O—*′, *—S—*′, *—N(Q₂₀₁)—*′, a substituted orunsubstituted C₁-C₂₀ alkylene group, a substituted or unsubstitutedC₂-C₂₀ alkenylene group, a substituted or unsubstituted C₃-C₁₀cycloalkylene group, a substituted or unsubstituted C₁-C₁₀heterocycloalkylene group, a substituted or unsubstituted C₃-C₁₀cycloalkenylene group, a substituted or unsubstituted C₁-C₁₀heterocycloalkenylene group, a substituted or unsubstituted C₆-C₆₀arylene group, a substituted or unsubstituted C₁-C₆₀ heteroarylenegroup, a substituted or unsubstituted divalent non-aromatic condensedpolycyclic group, and a substituted or unsubstituted divalentnon-aromatic condensed heteropolycyclic group,

xa1 to xa4 may each independently be an integer of 0 to 3,

xa5 may be an integer of 1 to 10, and

R₂₀₁ to R₂₀₄ and Q₂₀₁ may each independently be selected from asubstituted or unsubstituted C₃-C₁₀ cycloalkyl group, a substituted orunsubstituted C₁-C₁₀ heterocycloalkyl group, a substituted orunsubstituted C₃-C₁₀ cycloalkenyl group, a substituted or unsubstitutedC₁-C₁₀ heterocycloalkenyl group, a substituted or unsubstituted C₆-C₆₀aryl group, a substituted or unsubstituted C₆-C₆₀ aryloxy group, asubstituted or unsubstituted C₆-C₆₀ arylthio group, a substituted orunsubstituted C₁-C₆₀ heteroaryl group, a substituted or unsubstitutedmonovalent non-aromatic condensed polycyclic group, and a substituted orunsubstituted monovalent non-aromatic condensed heteropolycyclic group.

In one embodiment, in Formula 202, R₂₀₁ and R₂₀₂ may optionally belinked via a single bond, a dimethyl-methylene group, or adiphenyl-methylene group, and R₂₀₃ and R₂₀₄ may optionally be linked viaa single bond, a dimethyl-methylene group, or a diphenyl-methylenegroup.

In one embodiment, in Formulae 201 and 202,

L₂₀₁ to L₂₀₅ may each independently be selected from:

a phenylene group, a pentalenylene group, an indenylene group, anaphthylene group, an azulenylene group, a heptalenylene group, anindacenylene group, an acenaphthylene group, a fluorenylene group, aspiro-bifluorenylene group, a benzofluorenylene group, adibenzofluorenylene group, a phenalenylene group, a phenanthrenylenegroup, an anthracenylene group, a fluoranthenylene group, atriphenylenylene group, a pyrenylene group, a chrysenylene group, anaphthacenylene group, a picenylene group, a perylenylene group, apentaphenylene group, a hexacenylene group, a pentacenylene group, arubicenylene group, a coronenylene group, an ovalenylene group, athiophenylene group, a furanylene group, a carbazolylene group, anindolylene group, an isoindolylene group, a benzofuranylene group, abenzothiophenylene group, a dibenzofuranylene group, adibenzothiophenylene group, a benzocarbazolylene group, adibenzocarbazolylene group, a dibenzosilolylene group, and apyridinylene group; and

a phenylene group, a pentalenylene group, an indenylene group, anaphthylene group, an azulenylene group, a heptalenylene group, anindacenylene group, an acenaphthylene group, a fluorenylene group, aspiro-bifluorenylene group, a benzofluorenylene group, adibenzofluorenylene group, a phenalenylene group, a phenanthrenylenegroup, an anthracenylene group, a fluoranthenylene group, atriphenylenylene group, a pyrenylene group, a chrysenylene group, anaphthacenylene group, a picenylene group, a perylenylene group, apentaphenylene group, a hexacenylene group, a pentacenylene group, arubicenylene group, a coronenylene group, an ovalenylene group, athiophenylene group, a furanylene group, a carbazolylene group, anindolylene group, an isoindolylene group, a benzofuranylene group, abenzothiophenylene group, a dibenzofuranylene group, adibenzothiophenylene group, a benzocarbazolylene group, adibenzocarbazolylene group, a dibenzosilolylene group, and apyridinylene group, each substituted with at least one selected fromdeuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitrogroup, an amidino group, a hydrazino group, a hydrazono group, a C₁-C₂₀alkyl group, a C₁-C₂₀ alkoxy group, a cyclopentyl group, a cyclohexylgroup, a cycloheptyl group, a cyclopentenyl group, a cyclohexenyl group,a phenyl group, a biphenyl group, a terphenyl group, a phenyl groupsubstituted with a C₁-C₁₀ alkyl group, a phenyl group substituted with—F, a pentalenyl group, an indenyl group, a naphthyl group, an azulenylgroup, a heptalenyl group, an indacenyl group, an acenaphthyl group, afluorenyl group, a spiro-bifluorenyl group, a benzofluorenyl group, adibenzofluorenyl group, a phenalenyl group, a phenanthrenyl group, ananthracenyl group, a fluoranthenyl group, a triphenylenyl group, apyrenyl group, a chrysenyl group, a naphthacenyl group, a picenyl group,a perylenyl group, a pentaphenyl group, a hexacenyl group, a pentacenylgroup, a rubicenyl group, a coronenyl group, an ovalenyl group, athiophenyl group, a furanyl group, a carbazolyl group, an indolyl group,an isoindolyl group, a benzofuranyl group, a benzothiophenyl group, adibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolylgroup, a dibenzocarbazolyl group, a dibenzosilolyl group, a pyridinylgroup, —Si(Q₃₁)(Q₃₂)(Q₃₃), and —N(Q₃₁)(Q₃₂), and

Q₃₁ to Q₃₃ may each independently be selected from a C₁-C₁₀ alkyl group,a C₁-C₁₀ alkoxy group, a phenyl group, a biphenyl group, a terphenylgroup, and a naphthyl group.

In one or more embodiments, xa1 to xa4 may each independently be 0, 1,or 2.

In one or more embodiments, xa5 may be 1, 2, 3, or 4.

In one or more embodiments, R₂₀₁ to R₂₀₄ and Q₂₀₁ may each independentlybe selected from:

a phenyl group, a biphenyl group, a terphenyl group, a pentalenyl group,an indenyl group, a naphthyl group, an azulenyl group, a heptalenylgroup, an indacenyl group, an acenaphthyl group, a fluorenyl group, aspiro-bifluorenyl group, a benzofluorenyl group, a dibenzofluorenylgroup, a phenalenyl group, a phenanthrenyl group, an anthracenyl group,a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, achrysenyl group, a naphthacenyl group, a picenyl group, a perylenylgroup, a pentaphenyl group, a hexacenyl group, a pentacenyl group, arubicenyl group, a coronenyl group, an ovalenyl group, a thiophenylgroup, a furanyl group, a carbazolyl group, an indolyl group, anisoindolyl group, a benzofuranyl group, a benzothiophenyl group, adibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolylgroup, a dibenzocarbazolyl group, a dibenzosilolyl group, and apyridinyl group; and

a phenyl group, a biphenyl group, a terphenyl group, a pentalenyl group,an indenyl group, a naphthyl group, an azulenyl group, a heptalenylgroup, an indacenyl group, an acenaphthyl group, a fluorenyl group, aspiro-bifluorenyl group, a benzofluorenyl group, a dibenzofluorenylgroup, a phenalenyl group, a phenanthrenyl group, an anthracenyl group,a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, achrysenyl group, a naphthacenyl group, a picenyl group, a perylenylgroup, a pentaphenyl group, a hexacenyl group, a pentacenyl group, arubicenyl group, a coronenyl group, an ovalenyl group, a thiophenylgroup, a furanyl group, a carbazolyl group, an indolyl group, anisoindolyl group, a benzofuranyl group, a benzothiophenyl group, adibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolylgroup, a dibenzocarbazolyl group, a dibenzosilolyl group, and apyridinyl group, each substituted with at least one selected fromdeuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitrogroup, an amidino group, a hydrazino group, a hydrazono group, a C₁-C₂₀alkyl group, a C₁-C₂₀ alkoxy group, a cyclopentyl group, a cyclohexylgroup, a cycloheptyl group, a cyclopentenyl group, a cyclohexenyl group,a phenyl group, a biphenyl group, a terphenyl group, a phenyl groupsubstituted with a C₁-C₁₀ alkyl group, a phenyl group substituted with—F, a pentalenyl group, an indenyl group, a naphthyl group, an azulenylgroup, a heptalenyl group, an indacenyl group, an acenaphthyl group, afluorenyl group, a spiro-bifluorenyl group, a benzofluorenyl group, adibenzofluorenyl group, a phenalenyl group, a phenanthrenyl group, ananthracenyl group, a fluoranthenyl group, a triphenylenyl group, apyrenyl group, a chrysenyl group, a naphthacenyl group, a picenyl group,a perylenyl group, a pentaphenyl group, a hexacenyl group, a pentacenylgroup, a rubicenyl group, a coronenyl group, an ovalenyl group, athiophenyl group, a furanyl group, a carbazolyl group, an indolyl group,an isoindolyl group, a benzofuranyl group, a benzothiophenyl group, adibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolylgroup, a dibenzocarbazolyl group, a dibenzosilolyl group, a pyridinylgroup, —Si(Q₃₁)(Q₃₂)(Q₃₃), and —N(Q₃₁)(Q₃₂), and

Q₃₁ to Q₃₃ are the same as described herein above.

In one or more embodiments, in Formula 201, at least one selected fromR₂₀₁ to R₂₀₃ may each independently be selected from:

a fluorenyl group, a spiro-bifluorenyl group, a carbazolyl group, adibenzofuranyl group, and a dibenzothiophenyl group; and

a fluorenyl group, a spiro-bifluorenyl group, a carbazolyl group, adibenzofuranyl group, and a dibenzothiophenyl group, each substitutedwith at least one selected from deuterium, —F, —Cl, —Br, —I, a hydroxylgroup, a cyano group, a nitro group, an amidino group, a hydrazinogroup, a hydrazono group, a C₁-C₂₀ alkyl group, a C₁-C₂₀ alkoxy group, acyclopentyl group, a cyclohexyl group, a cycloheptyl group, acyclopentenyl group, a cyclohexenyl group, a phenyl group, a biphenylgroup, a terphenyl group, a phenyl group substituted with a C₁-C₁₀ alkylgroup, a phenyl group substituted with —F, a naphthyl group, a fluorenylgroup, a spiro-bifluorenyl group, a carbazolyl group, a dibenzofuranylgroup, and a dibenzothiophenyl group,

but embodiments of the present disclosure are not limited thereto.

In one or more embodiments, in Formula 202, i) R₂₀₁ and R₂₀₂ may belinked via a single bond, and/or ii) R₂₀₃ and R₂₀₄ may be linked via asingle bond.

In one or more embodiments, in Formula 202, at least one selected fromR₂₀₁ to R₂₀₄ may be selected from:

a carbazolyl group; and

a carbazolyl group substituted with at least one selected fromdeuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitrogroup, an amidino group, a hydrazino group, a hydrazono group, a C₁-C₂₀alkyl group, a C₁-C₂₀ alkoxy group, a cyclopentyl group, a cyclohexylgroup, a cycloheptyl group, a cyclopentenyl group, a cyclohexenyl group,a phenyl group, a biphenyl group, a terphenyl group, a phenyl groupsubstituted with a C₁-C₁₀ alkyl group, a phenyl group substituted with—F, a naphthyl group, a fluorenyl group, a spiro-bifluorenyl group, acarbazolyl group, a dibenzofuranyl group, and a dibenzothiophenyl group,

but embodiments of the present disclosure are not limited thereto.

The compound represented by Formula 201 may be represented by Formula201A:

In one embodiment, the compound represented by Formula 201 may berepresented by Formula 201A(1), but embodiments of the presentdisclosure are not limited thereto:

In one embodiment, the compound represented by Formula 201 may berepresented by Formula 201A-1, but embodiments of the present disclosureare not limited thereto:

In one embodiment, the compound represented by Formula 202 may berepresented by Formula 202A:

In one or more embodiments, the compound represented by Formula 202 maybe represented by Formula 202A-1:

In Formulae 201A, 201A(1), 201A-1, 202A, and 202A-1,

L₂₀₁ to L₂₀₃, xa1 to xa3, xa5, and R₂₀₂ to R₂₀₄ are the same asdescribed herein above,

R₂₁₁ and R₂₁₂ may each independently be the same as defined inconnection with R₂₀₃,

R₂₁₃ to R₂₁₇ may each independently be selected from hydrogen,deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitrogroup, an amidino group, a hydrazino group, a hydrazono group, a C₁-C₂₀alkyl group, a C₁-C₂₀ alkoxy group, a cyclopentyl group, a cyclohexylgroup, a cycloheptyl group, a cyclopentenyl group, a cyclohexenyl group,a phenyl group, a biphenyl group, a terphenyl group, a phenyl groupsubstituted with a C₁-C₁₀ alkyl group, a phenyl group substituted with—F, a pentalenyl group, an indenyl group, a naphthyl group, an azulenylgroup, a heptalenyl group, an indacenyl group, an acenaphthyl group, afluorenyl group, a spiro-bifluorenyl group, a benzofluorenyl group, adibenzofluorenyl group, a phenalenyl group, a phenanthrenyl group, ananthracenyl group, a fluoranthenyl group, a triphenylenyl group, apyrenyl group, a chrysenyl group, a naphthacenyl group, a picenyl group,a perylenyl group, a pentaphenyl group, a hexacenyl group, a pentacenylgroup, a rubicenyl group, a coronenyl group, an ovalenyl group, athiophenyl group, a furanyl group, a carbazolyl group, an indolyl group,an isoindolyl group, a benzofuranyl group, a benzothiophenyl group, adibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolylgroup, a dibenzocarbazolyl group, a dibenzosilolyl group, and apyridinyl group.

The hole transport region may include at least one compound selectedfrom Compounds HT1 to HT39, but embodiments of the present disclosureare not limited thereto:

A thickness of the hole transport region may be in a range of about 100Å to about 10,000 Å, for example, about 100 Å to about 1,000 Å. When thehole transport region includes at least one of a hole injection layerand a hole transport layer, a thickness of the hole injection layer maybe in a range of about 100 Å to about 9,000 Å, for example, about 100 Åto about 1,000 Å, and a thickness of the hole transport layer may be ina range of about 50 Å to about 2,000 Å, for example about 100 Å to about1,500 Å. When the thicknesses of the hole transport region, the holeinjection layer, and the hole transport layer are within these ranges,suitable or satisfactory hole transporting characteristics may beobtained without a substantial increase in driving voltage.

The emission auxiliary layer may increase light-emission efficiency bycompensating for an optical resonance distance according to thewavelength of light emitted by an emission layer, and the electronblocking layer may block the flow of electrons from an electrontransport region. The emission auxiliary layer and the electron blockinglayer may include the materials as described above.

p-Dopant

The hole transport region may further include, in addition toabove-described materials, a charge-generation material for theimprovement of conductive properties. The charge-generation material maybe homogeneously or non-homogeneously dispersed in the hole transportregion.

The charge-generation material may be, for example, a p-dopant.

In one embodiment, the p-dopant may have a lowest unoccupied molecularorbital (LUMO) level of about −3.5 eV or less.

The p-dopant may include at least one selected from a quinonederivative, a metal oxide, and a cyano group-containing compound, butembodiments of the present disclosure are not limited thereto.

For example, the p-dopant may include at least one selected from:

a quinone derivative, such as tetracyanoquinodimethane (TCNQ) or2,3,5,6-tetrafluoro-7,7,8,8-tetracyanoquinodimethane (F4-TCNQ);

a metal oxide, such as tungsten oxide or molybdenum oxide;

1,4,5,8,9,11-hexaazatriphenylene-hexacarbonitrile (HAT-CN); and

a compound represented by Formula 221:

but embodiments of the present disclosure are not limited thereto:

In Formula 221,

R₂₂₁ to R₂₂₃ may each independently be selected from a substituted orunsubstituted C₃-C₁₀ cycloalkyl group, a substituted or unsubstitutedC₁-C₁₀ heterocycloalkyl group, a substituted or unsubstituted C₃-C₁₀cycloalkenyl group, a substituted or unsubstituted C₁-C₁₀heterocycloalkenyl group, a substituted or unsubstituted C₆-C₆₀ arylgroup, a substituted or unsubstituted C₁-C₆₀ heteroaryl group, asubstituted or unsubstituted monovalent non-aromatic condensedpolycyclic group, and a substituted or unsubstituted monovalentnon-aromatic condensed heteropolycyclic group, wherein at least oneselected from R₂₂₁ to R₂₂₃ may include at least one substituent selectedfrom a cyano group, —F, —Cl, —Br, —I, a C₁-C₂₀ alkyl group substitutedwith —F, a C₁-C₂₀ alkyl group substituted with —Cl, a C₁-C₂₀ alkyl groupsubstituted with —Br, and a C₁-C₂₀ alkyl group substituted with —I.

Emission Layer in Organic Layer 150

When the organic light-emitting device 10 is a full-color organiclight-emitting device, the emission layer may be patterned into a redemission layer, a green emission layer, or a blue emission layer,according to a sub-pixel. In one or more embodiments, the emission layermay have a stacked structure of two or more layers selected from a redemission layer, a green emission layer, and a blue emission layer, inwhich the two or more layers contact each other or are separated fromeach other. In one or more embodiments, the emission layer may includetwo or more materials selected from a red light-emitting material, agreen light-emitting material, and a blue light-emitting material, inwhich the two or more materials are mixed with each other in a singlelayer to emit white light.

The emission layer may include a host and a dopant. The emission layermay include at least one selected from a phosphorescent dopant and afluorescent dopant.

In the emission layer, an amount of the dopant may be in a range ofabout 0.01 parts to about 15 parts by weight based on 100 parts byweight of the host, but embodiments of the present disclosure are notlimited thereto.

A thickness of the emission layer may be in a range of about 100 Å toabout 1,000 Å, for example, about 200 Å to about 600 Å. When thethickness of the emission layer is within this range, excellentlight-emission characteristics may be obtained without a substantialincrease in driving voltage.

Host in Emission Layer

In one or more embodiments, the host may include a compound representedby Formula 301:

[Ar₃₀₁]_(xb11)-[(L₃₀₁)_(xb1)-R₃₀₁]_(xb21)   Formula 301

In Formula 301,

Ar₃₀₁ may be a substituted or unsubstituted C₅-C₆₀ carbocyclic group ora substituted or unsubstituted C₁-C₆₀ heterocyclic group,

xb11 may be 1, 2, or 3,

L₃₀₁ may be selected from a substituted or unsubstituted C₃-C₁₀cycloalkylene group, a substituted or unsubstituted C₁-C₁₀heterocycloalkylene group, a substituted or unsubstituted C₃-C₁₀cycloalkenylene group, a substituted or unsubstituted C₁-C₁₀heterocycloalkenylene group, a substituted or unsubstituted C₆-C₆₀arylene group, a substituted or unsubstituted C₁-C₆₀ heteroarylenegroup, a substituted or unsubstituted divalent non-aromatic condensedpolycyclic group, and a substituted or unsubstituted divalentnon-aromatic condensed heteropolycyclic group,

xb1 may be an integer of 0 to 5,

R₃₀₁ may be selected from deuterium, —F, —Cl, —Br, —I, a hydroxyl group,a cyano group, a nitro group, an amidino group, a hydrazino group, ahydrazono group, a substituted or unsubstituted C₁-C₆₀ alkyl group, asubstituted or unsubstituted C₂-C₆₀ alkenyl group, a substituted orunsubstituted C₂-C₆₀ alkynyl group, a substituted or unsubstitutedC₁-C₆₀ alkoxy group, a substituted or unsubstituted C₃-C₁₀ cycloalkylgroup, a substituted or unsubstituted C₁-C₁₀ heterocycloalkyl group, asubstituted or unsubstituted C₃-C₁₀ cycloalkenyl group, a substituted orunsubstituted C₁-C₁₀ heterocycloalkenyl group, a substituted orunsubstituted C₆-C₆₀ aryl group, a substituted or unsubstituted C₆-C₆₀aryloxy group, a substituted or unsubstituted C₆-C₆₀ arylthio group, asubstituted or unsubstituted C₁-C₆₀ heteroaryl group, a substituted orunsubstituted monovalent non-aromatic condensed polycyclic group, asubstituted or unsubstituted monovalent non-aromatic condensedheteropolycyclic group, —Si(Q₃₀₁)(Q₃₀₂)(Q₃₀₃), —N(Q₃₀₁)(Q₃₀₂),—B(Q₃₀₁)(Q₃₀₂), —C(═O)(Q₃₀₁), —S(═O)₂(Q₃₀₁), and —P(═O)(Q₃₀₁)(Q₃₀₂),

xb21 may be an integer of 1 to 5, and

Q₃₀₁ to Q₃₀₃ may each independently be selected from a C₁-C₁₀ alkylgroup, a C₁-C₁₀ alkoxy group, a phenyl group, a biphenyl group, aterphenyl group, and a naphthyl group, but embodiments of the presentdisclosure are not limited thereto.

In one embodiment, in Formula 301, Ar₃₀₁ may be selected from:

a naphthalene group, a fluorene group, a spiro-bifluorene group, abenzofluorene group, a dibenzofluorene group, a phenalene group, aphenanthrene group, an anthracene group, a fluoranthene group, atriphenylene group, a pyrene group, a chrysene group, a naphthacenegroup, a picene group, a perylene group, a pentaphene group, anindenoanthracene group, a dibenzofuran group, and a dibenzothiophenegroup; and

a naphthalene group, a fluorene group, a spiro-bifluorene group, abenzofluorene group, a dibenzofluorene group, a phenalene group, aphenanthrene group, an anthracene group, a fluoranthene group, atriphenylene group, a pyrene group, a chrysene group, a naphthacenegroup, a picene group, a perylene group, a pentaphene group, anindenoanthracene group, a dibenzofuran group, and a dibenzothiophenegroup, each substituted with at least one selected from deuterium, —F,—Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidinogroup, a hydrazino group, a hydrazono group, a C₁-C₂₀ alkyl group, aC₁-C₂₀ alkoxy group, a phenyl group, a biphenyl group, a terphenylgroup, a naphthyl group, —Si(Q₃₁)(Q₃₂)(Q₃₃), —N(Q₃₁)(Q₃₂), —(Q₃₁)(Q₃₂),—C(═O)(Q₃₁), —S(═O)₂(Q₃₁), and —P(═O)(Q₃₁)(Q₃₂), and

Q₃₁ to Q₃₃ may each independently be selected from a C₁-C₁₀ alkyl group,a C₁-C₁₀ alkoxy group, a phenyl group, a biphenyl group, a terphenylgroup, and a naphthyl group, but embodiments of the present disclosureare not limited thereto.

When xb11 in Formula 301 is two or more, two or more Ar301(s) may belinked via a single bond.

In one or more embodiments, the compound represented by Formula 301 maybe represented by Formula 301-1 or 301-2:

In Formulae 301-1 and 301-2,

A₃₀₁ to A₃₀₄ may each independently be selected from a benzene group, anaphthalene group, a phenanthrene group, a fluoranthene group, atriphenylene group, a pyrene group, a chrysene group, a pyridine group,a pyrimidine group, an indene group, a fluorene group, aspiro-bifluorene group, a benzofluorene group, a dibenzofluorene group,an indole group, a carbazole group, a benzocarbazole group, adibenzocarbazole group, a furan group, a benzofuran group, adibenzofuran group, a naphthofuran group, a benzonaphthofuran group, adinaphthofuran group, a thiophene group, a benzothiophene group, adibenzothiophene group, a naphthothiophene group, abenzonaphthothiophene group and dinaphthothiophene group,

X₃₀₁ may be O, S, or N-[(L₃₀₄)_(xb4)-R₃₀₄],

R₃₁₁ to R₃₁₄ may each independently be selected from hydrogen,deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitrogroup, an amidino group, a hydrazino group, a hydrazono group, a C₁-C₂₀alkyl group, a C₁-C₂₀ alkoxy group, a phenyl group, a biphenyl group, aterphenyl group, a naphthyl group —Si(Q₃₁)(Q₃₂)(Q₃₃), —N(Q₃₁)(Q₃₂),—B(Q₃₁)(Q₃₂), —C(═O)(Q₃₁), —S(═O)₂(Q₃₁), and —P(═O)(Q₃₁)(Q₃₂),

xb22 and xb23 may each independently be 0, 1, or 2,

L₃₀₁, xb1, R₃₀₁, and Q₃₁ to Q₃₃ are the same as described herein above,

L₃₀₂ to L₃₀₄ may each independently be the same as defined in connectionwith L₃₀₁,

xb2 to xb4 may each independently be the same as defined in connectionwith xb1, and

R₃₀₂ to R₃₀₄ may each independently be the same as defined in connectionwith R₃₀₁.

For example, in Formulae 301, 301-1, and 301-2, L₃₀₁ to L₃₀₄ may eachindependently be selected from:

a phenylene group, a naphthylene group, a fluorenylene group, aspiro-bifluorenylene group, a benzofluorenylene group, adibenzofluorenylene group, a phenanthrenylene group, an anthracenylenegroup, a fluoranthenylene group, a triphenylenylene group, a pyrenylenegroup, a chrysenylene group, a perylenylene group, a pentaphenylenegroup, a hexacenylene group, a pentacenylene group, a thiophenylenegroup, a furanylene group, a carbazolylene group, an indolylene group,an isoindolylene group, a benzofuranylene group, a benzothiophenylenegroup, a dibenzofuranylene group, a dibenzothiophenylene group, abenzocarbazolylene group, a dibenzocarbazolylene group, adibenzosilolylene group, a pyridinylene group, an imidazolylene group, apyrazolylene group, a thiazolylene group, an isothiazolylene group, anoxazolylene group, an isoxazolylene group, a thiadiazolylene group, anoxadiazolylene group, a pyrazinylene group, a pyrimidinylene group, apyridazinylene group, a triazinylene group, a quinolinylene group, anisoquinolinylene group, a benzoquinolinylene group, a phthalazinylenegroup, a naphthyridinylene group, a quinoxalinylene group, aquinazolinylene group, a cinnolinylene group, a phenanthridinylenegroup, an acridinylene group, a phenanthrolinylene group, aphenazinylene group, a benzimidazolylene group, an isobenzothiazolylenegroup, a benzoxazolylene group, an isobenzoxazolylene group, atriazolylene group, a tetrazolylene group, an imidazopyridinylene group,an imidazopyrimidinylene group, and an azacarbazolylene group; and

a phenylene group, a naphthylene group, a fluorenylene group, aspiro-bifluorenylene group, a benzofluorenylene group, adibenzofluorenylene group, a phenanthrenylene group, an anthracenylenegroup, a fluoranthenylene group, a triphenylenylene group, a pyrenylenegroup, a chrysenylene group, a perylenylene group, a pentaphenylenegroup, a hexacenylene group, a pentacenylene group, a thiophenylenegroup, a furanylene group, a carbazolylene group, an indolylene group,an isoindolylene group, a benzofuranylene group, a benzothiophenylenegroup, a dibenzofuranylene group, a dibenzothiophenylene group, abenzocarbazolylene group, a dibenzocarbazolylene group, adibenzosilolylene group, a pyridinylene group, an imidazolylene group, apyrazolylene group, a thiazolylene group, an isothiazolylene group, anoxazolylene group, an isoxazolylene group, a thiadiazolylene group, anoxadiazolylene group, a pyrazinylene group, a pyrimidinylene group, apyridazinylene group, a triazinylene group, a quinolinylene group, anisoquinolinylene group, a benzoquinolinylene group, a phthalazinylenegroup, a naphthyridinylene group, a quinoxalinylene group, aquinazolinylene group, a cinnolinylene group, a phenanthridinylenegroup, an acridinylene group, a phenanthrolinylene group, aphenazinylene group, a benzimidazolylene group, an isobenzothiazolylenegroup, a benzoxazolylene group, an isobenzoxazolylene group, atriazolylene group, a tetrazolylene group, an imidazopyridinylene group,an imidazopyrimidinylene group, and an azacarbazolylene group, eachsubstituted with at least one selected from deuterium, —F, —Cl, —Br, —I,a hydroxyl group, a cyano group, a nitro group, an amidino group, ahydrazino group, a hydrazono group, a C₁-C₂₀ alkyl group, a C₁-C₂₀alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, anaphthyl group, a fluorenyl group, a spiro-bifluorenyl group, abenzofluorenyl group, a dibenzofluorenyl group, a phenanthrenyl group,an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, apyrenyl group, a chrysenyl group, a perylenyl group, a pentaphenylgroup, a hexacenyl group, a pentacenyl group, a thiophenyl group, afuranyl group, a carbazolyl group, an indolyl group, an isoindolylgroup, a benzofuranyl group, a benzothiophenyl group, a dibenzofuranylgroup, a dibenzothiophenyl group, a benzocarbazolyl group, adibenzocarbazolyl group, a dibenzosilolyl group, a pyridinyl group, animidazolyl group, a pyrazolyl group, a thiazolyl group, an isothiazolylgroup, an oxazolyl group, an isoxazolyl group, a thiadiazolyl group, anoxadiazolyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinylgroup, a triazinyl group, a quinolinyl group, an isoquinolinyl group, abenzoquinolinyl group, a phthalazinyl group, a naphthyridinyl group, aquinoxalinyl group, a quinazolinyl group, a cinnolinyl group, aphenanthridinyl group, an acridinyl group, a phenanthrolinyl group, aphenazinyl group, a benzimidazolyl group, an isobenzothiazolyl group, abenzoxazolyl group, an isobenzoxazolyl group, a triazolyl group, atetrazolyl group, an imidazopyridinyl group, an imidazopyrimidinylgroup, an azacarbazolyl group, —Si(Q₃₁)(Q₃₂)(Q₃₃), —N(Q₃₁)(Q₃₂),—B(Q₃₁)(Q₃₂), —C(═O)(Q₃₁), —S(═O)₂(Q₃₁), and —P(═O)(Q₃₁)(Q₃₂), and

Q₃₁ to Q₃₃ are the same as described herein above.

In one embodiment, in Formulae 301, 301-1, and 301-2, R₃₀₁ to R₃₀₄ mayeach independently be selected from:

a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, afluorenyl group, a spiro-bifluorenyl group, a benzofluorenyl group, adibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, afluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenylgroup, a perylenyl group, a pentaphenyl group, a hexacenyl group, apentacenyl group, a thiophenyl group, a furanyl group, a carbazolylgroup, an indolyl group, an isoindolyl group, a benzofuranyl group, abenzothiophenyl group, a dibenzofuranyl group, a dibenzothiophenylgroup, a benzocarbazolyl group, a dibenzocarbazolyl group, adibenzosilolyl group, a pyridinyl group, an imidazolyl group, apyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolylgroup, an isoxazolyl group, a thiadiazolyl group, an oxadiazolyl group,a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a triazinylgroup, a quinolinyl group, an isoquinolinyl group, a benzoquinolinylgroup, a phthalazinyl group, a naphthyridinyl group, a quinoxalinylgroup, a quinazolinyl group, a cinnolinyl group, a phenanthridinylgroup, an acridinyl group, a phenanthrolinyl group, a phenazinyl group,a benzimidazolyl group, an isobenzothiazolyl group, a benzoxazolylgroup, an isobenzoxazolyl group, a triazolyl group, a tetrazolyl group,an imidazopyridinyl group, an imidazopyrimidinyl group, and anazacarbazolyl group; and

a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, afluorenyl group, a spiro-bifluorenyl group, a benzofluorenyl group, adibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, afluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenylgroup, a perylenyl group, a pentaphenyl group, a hexacenyl group, apentacenyl group, a thiophenyl group, a furanyl group, a carbazolylgroup, an indolyl group, an isoindolyl group, a benzofuranyl group, abenzothiophenyl group, a dibenzofuranyl group, a dibenzothiophenylgroup, a benzocarbazolyl group, a dibenzocarbazolyl group, adibenzosilolyl group, a pyridinyl group, an imidazolyl group, apyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolylgroup, an isoxazolyl group, a thiadiazolyl group, an oxadiazolyl group,a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a triazinylgroup, a quinolinyl group, an isoquinolinyl group, a benzoquinolinylgroup, a phthalazinyl group, a naphthyridinyl group, a quinoxalinylgroup, a quinazolinyl group, a cinnolinyl group, a phenanthridinylgroup, an acridinyl group, a phenanthrolinyl group, a phenazinyl group,a benzimidazolyl group, an isobenzothiazolyl group, a benzoxazolylgroup, an isobenzoxazolyl group, a triazolyl group, a tetrazolyl group,an imidazopyridinyl group, an imidazopyrimidinyl group, and anazacarbazolyl group, each substituted with at least one selected fromdeuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitrogroup, an amidino group, a hydrazino group, a hydrazono group, a C₁-C₂₀alkyl group, a C₁-C₂₀ alkoxy group, a phenyl group, a biphenyl group, aterphenyl group, a naphthyl group, a fluorenyl group, aspiro-bifluorenyl group, a benzofluorenyl group, a dibenzofluorenylgroup, a phenanthrenyl group, an anthracenyl group, a fluoranthenylgroup, a triphenylenyl group, a pyrenyl group, a chrysenyl group, aperylenyl group, a pentaphenyl group, a hexacenyl group, a pentacenylgroup, a thiophenyl group, a furanyl group, a carbazolyl group, anindolyl group, an isoindolyl group, a benzofuranyl group, abenzothiophenyl group, a dibenzofuranyl group, a dibenzothiophenylgroup, a benzocarbazolyl group, a dibenzocarbazolyl group, adibenzosilolyl group, a pyridinyl group, an imidazolyl group, apyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolylgroup, an isoxazolyl group, a thiadiazolyl group, an oxadiazolyl group,a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a triazinylgroup, a quinolinyl group, an isoquinolinyl group, a benzoquinolinylgroup, a phthalazinyl group, a naphthyridinyl group, a quinoxalinylgroup, a quinazolinyl group, a cinnolinyl group, a phenanthridinylgroup, an acridinyl group, a phenanthrolinyl group, a phenazinyl group,a benzimidazolyl group, an isobenzothiazolyl group, a benzoxazolylgroup, an isobenzoxazolyl group, a triazolyl group, a tetrazolyl group,an imidazopyridinyl group, an imidazopyrimidinyl group, an azacarbazolylgroup, —Si(Q₃₁)(Q₃₂)(Q₃₃), —N(Q₃₁)(Q₃₂), —B(Q₃₁)(Q₃₂), —C(═O)(Q₃₁),—S(═O)₂(Q₃₁), and —P(═O)(Q₃₁)(Q₃₂), and

Q₃₁ to Q₃₃ are the same as described herein above.

In one embodiment, the host may include an alkaline earth metal complex.For example, the host may be selected from a Be complex (for example,Compound H55), a Mg complex, and a Zn complex.

The host may include at least one selected from9,10-di(2-naphthyl)anthracene (ADN),2-methyl-9,10-bis(naphthalen-2-yl)anthracene (MADN),9,10-di-(2-naphthyl)-2-t-butyl-anthracene (TBADN),4,4′-bis(N-carbazolyl)-1,1′-biphenyl (CBP), mCP(1,3-di-9-carbazolylbenzene), 1,3,5-tri(carbazol-9-yl)benzene) TCP),bis(4-(9H-carbazol-9-yl)phenyl)diphenylsilane (BCPDS),4-(1-(4-(diphenylamino)phenyl)cyclohexyl)phenyl)diphenyl-phosphine oxide(POPCPA), and Compounds H1 to H55, but embodiments of the presentdisclosure are not limited thereto:

In one embodiment, the host may include at least one selected from asilicon-containing compound (for example, BCPDS used in the followingexamples or the like) and a phosphine oxide-containing compound (forexample, POPCPA used in the following examples or the like).

However, embodiments of the present disclosure are not limited thereto.In one embodiment, the host may include only one compound, or two ormore different compounds (for example, a host used in the followingexamples includes BCPDS and POPCPA).

[Phosphorescent Dopant Included in Emission Layer in Organic Layer 150]

The phosphorescent dopant may include an organometallic complexrepresented by Formula 401:

In Formulae 401 and 402,

M may be selected from iridium (Ir), platinum (Pt), palladium (Pd),osmium (Os), titanium (Ti), zirconium (Zr), hafnium (Hf), europium (Eu),terbium (Tb), rhodium (Rh), and thulium (Tm),

L₄₀₁ may be selected from ligands represented by Formula 402, and xc1may be 1, 2, or 3, wherein, when xc1 is two or more, two or more L₄₀₁(s)may be identical to or different from each other,

L₄₀₂ may be an organic ligand, and xc2 may be an integer of 0 to 4,wherein, when xc2 is two or more, two or more L₄₀₂(s) may be identicalto or different from each other,

X₄₀₁ to X₄₀₄ may each independently be nitrogen or carbon,

X₄₀₁ and X₄₀₃ may be linked via a single bond or a double bond, and X₄₀₂and X₄₀₄ may be linked via a single bond or a double bond,

A₄₀₁ and A₄₀₂ may each independently be a C₅-C₆₀carbocyclic group or aC₁-C₆₀ heterocyclic group,

X₄₀₅ may be a single bond, *—O—*′, *—S—*′, *—C(═O)—*′, *—N(Q₄₁₁)—*′,*—C(Q₄₁₁)(Q₄₁₂)—*′, *—C(Q₄₁₁)═C(Q₄₁₂)—*′, *—C(Q₄₁₁)═*′, or *═C(Q₄₁₁)═*′,wherein Q₄₁₁ and Q₄₁₂ may be hydrogen, deuterium, a C₁-C₂₀ alkyl group,a C₁-C₂₀ alkoxy group, a phenyl group, a biphenyl group, a terphenylgroup, or a naphthyl group,

X₄₀₆ may be a single bond, O, or S,

R₄₀₁ and R₄₀₂ may each independently be selected from hydrogen,deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitrogroup, an amidino group, a hydrazino group, a hydrazono group, asubstituted or unsubstituted C₁-C₂₀ alkyl group, a substituted orunsubstituted C₁-C₂₀ alkoxy group, a substituted or unsubstituted C₃-C₁₀cycloalkyl group, a substituted or unsubstituted C₁-C₁₀ heterocycloalkylgroup, a substituted or unsubstituted C₃-C₁₀ cycloalkenyl group, asubstituted or unsubstituted C₁-C₁₀ heterocycloalkenyl group, asubstituted or unsubstituted C₆-C₆₀ aryl group, a substituted orunsubstituted C₆-C₆₀ aryloxy group, a substituted or unsubstitutedC₆-C₆₀ arylthio group, a substituted or unsubstituted C₁-C₆₀ heteroarylgroup, a substituted or unsubstituted monovalent non-aromatic condensedpolycyclic group, and a substituted or unsubstituted monovalentnon-aromatic condensed heteropolycyclic group, —Si(Q₄₀₁)(Q₄₀₂)(Q₄₀₃),—N(Q₄₀₁)(Q₄₀₂), —B(Q₄₀₁)(Q₄₀₂), —C(═O)(Q₄₀₁), —S(═O)₂(Q₄₀₁), and—P(═O)(Q₄₀₁)(Q₄₀₂), wherein Q₄₀₁ to Q₄₀₃ may each independently beselected from a C₁-C₁₀ alkyl group, a C₁-C₁₀ alkoxy group, a C₆-C₂₀ arylgroup, and a C₁-C₂₀ heteroaryl group,

xc11 and xc12 may each independently be an integer of 0 to 10, and

* and *′ in Formula 402 each indicate a binding site to M in Formula401.

In one embodiment, in Formula 402, A₄₀₁ and A₄₀₂ may each independentlybe selected from a benzene group, a naphthalene group, a fluorene group,a spiro-bifluorene group, an indene group, a pyrrole group, a thiophenegroup, a furan group, an imidazole group, a pyrazole group, a thiazolegroup, an isothiazole group, an oxazole group, an isoxazole group, apyridine group, a pyrazine group, a pyrimidine group, a pyridazinegroup, a quinoline group, an isoquinoline group, a benzoquinoline group,a quinoxaline group, a quinazoline group, a carbazole group, abenzimidazole group, a benzofuran group, a benzothiophene group, anisobenzothiophene group, a benzoxazole group, an isobenzoxazole group, atriazole group, a tetrazole group, an oxadiazole group, a triazinegroup, a dibenzofuran group, and a dibenzothiophene group.

In one or more embodiments, in Formula 402, i) X₄₀₁ may be nitrogen, andX₄₀₂ may be carbon, or ii) X₄₀₁ and X₄₀₂ may be both nitrogen.

In one or more embodiments, in Formula 402, R₄₀₁ and R₄₀₂ may eachindependently be selected from:

hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group,a nitro group, an amidino group, a hydrazino group, a hydrazono group, aC₁-C₂₀ alkyl group, and a C₁-C₂₀ alkoxy group;

a C₁-C₂₀ alkyl group, and a C₁-C₂₀ alkoxy group, each substituted withat least one selected from deuterium, —F, —Cl, —Br, —I, a hydroxylgroup, a cyano group, a nitro group, an amidino group, a hydrazinogroup, a hydrazono group, a phenyl group, a naphthyl group, acyclopentyl group, a cyclohexyl group, an adamantanyl group, anorbornanyl group, and a norbornenyl group;

a cyclopentyl group, a cyclohexyl group, an adamantanyl group, anorbornanyl group, a norbornenyl group, a phenyl group, a biphenylgroup, a terphenyl group, a naphthyl group, a fluorenyl group, apyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinylgroup, a triazinyl group, a quinolinyl group, an isoquinolinyl group, aquinoxalinyl group, a quinazolinyl group, a carbazolyl group, adibenzofuranyl group, and a dibenzothiophenyl group;

a cyclopentyl group, a cyclohexyl group, an adamantanyl group, anorbornanyl group, a norbornenyl group a phenyl group, a biphenyl group,a terphenyl group, a naphthyl group, a fluorenyl group, a pyridinylgroup, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, atriazinyl group, a quinolinyl group, an isoquinolinyl group, aquinoxalinyl group, a quinazolinyl group, a carbazolyl group, adibenzofuranyl group, and a dibenzothiophenyl group, each substitutedwith at least one selected from deuterium, —F, —Cl, —Br, —I, a hydroxylgroup, a cyano group, a nitro group, an amidino group, a hydrazinogroup, a hydrazono group, a C₁-C₂₀ alkyl group, a C₁-C₂₀ alkoxy group, acyclopentyl group, a cyclohexyl group, an adamantanyl group, anorbornanyl group, a norbornenyl group, a phenyl group, a biphenylgroup, a terphenyl group, a naphthyl group, a fluorenyl group, apyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinylgroup, a triazinyl group, a quinolinyl group, an isoquinolinyl group, aquinoxalinyl group, a quinazolinyl group, a carbazolyl group, adibenzofuranyl group, and a dibenzothiophenyl group; and

—Si(Q₄₀₁)(Q₄₀₂)(Q₄₀₃), —N(Q₄₀₁)(Q₄₀₂), —B(Q₄₀₁)(Q₄₀₂), —C(═O)(Q₄₀₁),—S(═O)₂(Q₄₀₁), and —P(═O)(Q₄₀₁)(Q₄₀₂), and

Q₄₀₁ to Q₄₀₃ may each independently be selected from a C₁-C₁₀ alkylgroup, a C₁-C₁₀ alkoxy group, a phenyl group, a biphenyl group, and anaphthyl group, but embodiments of the present disclosure are notlimited thereto.

In one or more embodiments, when xc1 in Formula 401 is two or more, twoA₄₀₁(s) in two or more L₄₀₁(s) may optionally be linked via X₄₀₇, whichis a linking group, or two A₄₀₂(s) in two or more L₄₀₁(s) may optionallybe linked via X₄₀₈, which is a linking group (see Compounds PD1 to PD4and PD7). X₄₀₇ and X₄₀₈ may each independently be a single bond, *—O—*′,*—S—*′, *—C(═O)—*′, *—N(Q₄₁₃)—*′, *—C(Q₄₁₃)(Q₄₁₄)—*′, or*—C(Q₄₁₃)═C(Q₄₁₄)—*′ (wherein Q₄₁₃ and Q₄₁₄ may each independently behydrogen, deuterium, a C₁-C₂₀ alkyl group, a C₁-C₂₀ alkoxy group, aphenyl group, a biphenyl group, a terphenyl group, or a naphthyl group),but embodiments of the present disclosure are not limited thereto.

L₄₀₂ in Formula 401 may be a monovalent, divalent, or trivalent organicligand. For example, L₄₀₂ may be selected from halogen, diketone (forexample, acetylacetonate), carboxylic acid (for example, picolinate),—C(═O), isonitrile, —CN, and phosphorus (for example, phosphine, orphosphite), but embodiments of the present disclosure are not limitedthereto.

In one or more embodiments, the phosphorescent dopant may be selectedfrom, for example, Compounds PD1 to PD25, but embodiments of the presentdisclosure are not limited thereto:

Fluorescent Dopant in Emission Layer of Organic Layer 150

The fluorescent dopant may include an arylamine compound or astyrylamine compound.

The fluorescent dopant may include a compound represented by Formula501:

In Formula 501,

Ar₅₀₁ may be a substituted or unsubstituted C₅-C₆₀ carbocyclic group ora substituted or unsubstituted C₁-C₆₀ heterocyclic group,

L₅₀₁ to L₅₀₃ may each independently be selected from a substituted orunsubstituted C₃-C₁₀ cycloalkylene group, a substituted or unsubstitutedC₁-C₁₀ heterocycloalkylene group, a substituted or unsubstituted C₃-C₁₀cycloalkenylene group, a substituted or unsubstituted C₁-C₁₀heterocycloalkenylene group, a substituted or unsubstituted C₆-C₆₀arylene group, a substituted or unsubstituted C₁-C₆₀ heteroarylenegroup, a substituted or unsubstituted divalent non-aromatic condensedpolycyclic group, and a substituted or unsubstituted divalentnon-aromatic condensed heteropolycyclic group,

xd1 to xd3 may each independently be an integer of 0 to 3,

R₅₀₁ and R₅₀₂ may each independently be selected from a substituted orunsubstituted C₃-C₁₀ cycloalkyl group, a substituted or unsubstitutedC₁-C₁₀ heterocycloalkyl group, a substituted or unsubstituted C₃-C₁₀cycloalkenyl group, a substituted or unsubstituted C₁-C₁₀heterocycloalkenyl group, a substituted or unsubstituted C₆-C₆₀ arylgroup, a substituted or unsubstituted C₆-C₆₀ aryloxy group, asubstituted or unsubstituted C₆-C₆₀ arylthio group, a substituted orunsubstituted C₁-C₆₀ heteroaryl group, a substituted or unsubstitutedmonovalent non-aromatic condensed polycyclic group, and a substituted orunsubstituted monovalent non-aromatic condensed heteropolycyclic group,and

xd4 may be an integer of 1 to 6.

In one embodiment, Ar₅₀₁ in Formula 501 may be selected from:

a naphthalene group, a heptalene group, a fluorene group, aspiro-bifluorene group, a benzofluorene group, a dibenzofluorene group,a phenalene group, a phenanthrene group, an anthracene group, afluoranthene group, a triphenylene group, a pyrene group, a chrysenegroup, a naphthacene group, a picene group, a perylene group, apentaphene group, an indenoanthracene group, and an indenophenanthrenegroup; and

a naphthalene group, a heptalene group, a fluorene group, aspiro-bifluorene group, a benzofluorene group, a dibenzofluorene group,a phenalene group, a phenanthrene group, an anthracene group, afluoranthene group, a triphenylene group, a pyrene group, a chrysenegroup, a naphthacene group, a picene group, a perylene group, apentaphene group, an indenoanthracene group, and an indenophenanthrenegroup, each substituted with at least one selected from deuterium, —F,—Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidinogroup, a hydrazino group, a hydrazono group, a C₁-C₂₀ alkyl group, aC₁-C₂₀ alkoxy group, a phenyl group, a biphenyl group, a terphenylgroup, and a naphthyl group.

In one or more embodiments, L₅₀₁ to L₅₀₃ in Formula 501 may eachindependently be selected from:

a phenylene group, a naphthylene group, a fluorenylene group, aspiro-bifluorenylene group, a benzofluorenylene group, adibenzofluorenylene group, a phenanthrenylene group, an anthracenylenegroup, a fluoranthenylene group, a triphenylenylene group, a pyrenylenegroup, a chrysenylene group, a perylenylene group, a pentaphenylenegroup, a hexacenylene group, a pentacenylene group, a thiophenylenegroup, a furanylene group, a carbazolylene group, an indolylene group,an isoindolylene group, a benzofuranylene group, a benzothiophenylenegroup, a dibenzofuranylene group, a dibenzothiophenylene group, abenzocarbazolylene group, a dibenzocarbazolylene group, adibenzosilolylene group, and a pyridinylene group; and

a phenylene group, a naphthylene group, a fluorenylene group, aspiro-bifluorenylene group, a benzofluorenylene group, adibenzofluorenylene group, a phenanthrenylene group, an anthracenylenegroup, a fluoranthenylene group, a triphenylenylene group, a pyrenylenegroup, a chrysenylene group, a perylenylene group, a pentaphenylenegroup, a hexacenylene group, a pentacenylene group, a thiophenylenegroup, a furanylene group, a carbazolylene group, an indolylene group,an isoindolylene group, a benzofuranylene group, a benzothiophenylenegroup, a dibenzofuranylene group, a dibenzothiophenylene group, abenzocarbazolylene group, a dibenzocarbazolylene group, adibenzosilolylene group, and a pyridinylene group, each substituted withat least one selected from deuterium, —F, —Cl, —Br, —I, a hydroxylgroup, a cyano group, a nitro group, an amidino group, a hydrazinogroup, a hydrazono group, a C₁-C₂₀ alkyl group, a C₁-C₂₀ alkoxy group, aphenyl group, a biphenyl group, a terphenyl group, a naphthyl group, afluorenyl group, a spiro-bifluorenyl group, a benzofluorenyl group, adibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, afluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenylgroup, a perylenyl group, a pentaphenyl group, a hexacenyl group, apentacenyl group, a thiophenyl group, a furanyl group, a carbazolylgroup, an indolyl group, an isoindolyl group, a benzofuranyl group, abenzothiophenyl group, a dibenzofuranyl group, a dibenzothiophenylgroup, a benzocarbazolyl group, a dibenzocarbazolyl group, adibenzosilolyl group, and a pyridinyl group.

In one or more embodiments, R₅₀₁ and R₅₀₂ in Formula 501 may eachindependently be selected from:

a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, afluorenyl group, a spiro-bifluorenyl group, a benzofluorenyl group, adibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, afluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenylgroup, a perylenyl group, a pentaphenyl group, a hexacenyl group, apentacenyl group, a thiophenyl group, a furanyl group, a carbazolylgroup, an indolyl group, an isoindolyl group, a benzofuranyl group, abenzothiophenyl group, a dibenzofuranyl group, a dibenzothiophenylgroup, a benzocarbazolyl group, a dibenzocarbazolyl group, adibenzosilolyl group, and a pyridinyl group; and

a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, afluorenyl group, a spiro-bifluorenyl group, a benzofluorenyl group, adibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, afluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenylgroup, a perylenyl group, a pentaphenyl group, a hexacenyl group, apentacenyl group, a thiophenyl group, a furanyl group, a carbazolylgroup, an indolyl group, an isoindolyl group, a benzofuranyl group, abenzothiophenyl group, a dibenzofuranyl group, a dibenzothiophenylgroup, a benzocarbazolyl group, a dibenzocarbazolyl group, adibenzosilolyl group, and a pyridinyl group, each substituted with atleast one selected from deuterium, —F, —Cl, —Br, —I, a hydroxyl group, acyano group, a nitro group, an amidino group, a hydrazino group, ahydrazono group, a C₁-C₂₀ alkyl group, a C₁-C₂₀ alkoxy group, a phenylgroup, a biphenyl group, a terphenyl group, a naphthyl group, afluorenyl group, a spiro-bifluorenyl group, a benzofluorenyl group, adibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, afluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenylgroup, a perylenyl group, a pentaphenyl group, a hexacenyl group, apentacenyl group, a thiophenyl group, a furanyl group, a carbazolylgroup, an indolyl group, an isoindolyl group, a benzofuranyl group, abenzothiophenyl group, a dibenzofuranyl group, a dibenzothiophenylgroup, a benzocarbazolyl group, a dibenzocarbazolyl group, adibenzosilolyl group, a pyridinyl group and —Si(Q₃₁)(Q₃₂)(Q₃₃), and

Q₃₁ to Q₃₃ may each independently be selected from a C₁-C₁₀ alkyl group,a C₁-C₁₀ alkoxy group, a phenyl group, a biphenyl group, a terphenylgroup, and a naphthyl group.

In one or more embodiments, xd4 in Formula 501 may be 2, but embodimentsof the present disclosure are not limited thereto.

For example, the fluorescent dopant may be selected from Compounds FD1to FD22:

In one or more embodiments, the fluorescent dopant may be selected fromthe following compounds, but embodiments of the present disclosure arenot limited thereto.

Electron Transport Region in Organic Layer 150

The electron transport region may have i) a single-layered structureincluding a single layer including a single material, ii) asingle-layered structure including a single layer including a pluralityof different materials, or iii) a multi-layered structure having aplurality of layers including a plurality of different materials.

The electron transport region may include at least one selected from abuffer layer, a hole blocking layer, an electron control layer, anelectron transport layer, and an electron injection layer, butembodiments of the present disclosure are not limited thereto.

For example, the electron transport region may have an electrontransport layer/electron injection layer structure, a hole blockinglayer/electron transport layer/electron injection layer structure, anelectron control layer/electron transport layer/electron injection layerstructure, or a buffer layer/electron transport layer/electron injectionlayer structure, wherein for each structure, constituting layers aresequentially stacked from an emission layer. However, embodiments of thestructure of the electron transport region are not limited thereto.

The electron transport region (for example, a buffer layer, a holeblocking layer, an electron control layer, or an electron transportlayer in the electron transport region) may include a metal-freecompound containing at least one 7 electron-depleted nitrogen-containingring.

As used herein, the term “π electron-depleted nitrogen-containing ring”refers to a C₁-C₆₀ heterocyclic group having at least one *—N═*′ moietyas a ring-forming moiety.

For example, the “π electron-depleted nitrogen-containing ring” may bei) a 5-membered to 7-membered heteromonocyclic group having at least one*—N═*′ moiety, ii) a heteropolycyclic group in which two or more5-membered to 7-membered heteromonocyclic groups each having at leastone *—N═*′ moiety are condensed with each other, or iii) aheteropolycyclic group in which at least one of 5-membered to 7-memberedheteromonocyclic groups, each having at least one *—N═*′ moiety, iscondensed with at least one C₅-C₆₀ carbocyclic group.

Examples of the π electron-depleted nitrogen-containing ring include animidazole group, a pyrazole group, a thiazole group, an isothiazolegroup, an oxazole group, an isoxazole group, a pyridine group, apyrazine group, a pyrimidine group, a pyridazine group, an indazolegroup, a purine group, a quinoline group, an isoquinoline group, abenzoquinoline group, a phthalazine group, a naphthyridine group, aquinoxaline group, a quinazoline group, a cinnoline group, aphenanthridine group, an acridine group, a phenanthroline group, aphenazine group, a benzimidazole group, an isobenzothiazole group, abenzoxazole group, an isobenzoxazole group, a triazole group, atetrazole group, an oxadiazole group, a triazine group, a thiadiazolgroup, an imidazopyridine group, an imidazopyrimidine group, and anazacarbazole group, but are not limited thereto.

For example, the electron transport region may include a compoundrepresented by Formula 601:

[Ar₆₀₁]_(xe11)-[(L₆₀₁)_(xe1)-R₆₀₁]_(xe21).   Formula 601

In Formula 601,

Ar₆₀₁ may be a substituted or unsubstituted C₅-C₆₀ carbocyclic group ora substituted or unsubstituted C₁-C₆₀ heterocyclic group,

xe11 may be 1, 2, or 3,

L₆₀₁ is selected from a substituted or unsubstituted C₃-C₁₀cycloalkylene group, a substituted or unsubstituted C₁-C₁₀heterocycloalkylene group, a substituted or unsubstituted C₃-C₁₀cycloalkenylene group, a substituted or unsubstituted C₁-C₁₀heterocycloalkenylene group, a substituted or unsubstituted C₆-C₆₀arylene group, a substituted or unsubstituted C₁-C₆₀ heteroarylenegroup, a substituted or unsubstituted divalent non-aromatic condensedpolycyclic group, and a substituted or unsubstituted divalentnon-aromatic condensed heteropolycyclic group,

xe1 may be an integer of 0 to 5,

R₆₀₁ may be selected from a substituted or unsubstituted C₃-C₁₀cycloalkyl group, a substituted or unsubstituted C₁-C₁₀ heterocycloalkylgroup, a substituted or unsubstituted C₃-C₁₀ cycloalkenyl group, asubstituted or unsubstituted C₁-C₁₀ heterocycloalkenyl group, asubstituted or unsubstituted C₆-C₆₀ aryl group, a substituted orunsubstituted C₆-C₆₀ aryloxy group, a substituted or unsubstitutedC₆-C₆₀ arylthio group, a substituted or unsubstituted C₁-C₆₀ heteroarylgroup, a substituted or unsubstituted monovalent non-aromatic condensedpolycyclic group, a substituted or unsubstituted monovalent non-aromaticcondensed heteropolycyclic group, —Si(Q₆₀₁)(Q₆₀₂)(Q₆₀₃), —C(═O)(Q₆₀₁),—S(═O)₂(Q₆₀₁), and —P(═O)(Q₆₀₁)(Q₆₀₂),

Q₆₀₁ to Q₆₀₃ may each independently be a C₁-C₁₀ alkyl group, a C₁-C₁₀alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, or anaphthyl group, and

xe21 may be an integer of 1 to 5.

In one embodiment, at least one of Ar₆₀₁(s) in the number of xe11 andR₆₀₁(s) in the number of xe21 may include the π electron-depletednitrogen-containing ring.

In one embodiment, ring Ar₆₀₁ in Formula 601 may be selected from:

a benzene group, a naphthalene group, a fluorene group, aspiro-bifluorene group, a benzofluorene group, a dibenzofluorene group,a phenalene group, a phenanthrene group, an anthracene group, afluoranthene group, a triphenylene group, a pyrene group, a chrysenegroup, a naphthacene group, a picene group, a perylene group, apentaphene group, an indenoanthracene group, a dibenzofuran group, adibenzothiophene group, a carbazole group, an imidazole group, apyrazole group, a thiazole group, an isothiazole group, an oxazolegroup, an isoxazole group, a pyridine group, a pyrazine group, apyrimidine group, a pyridazine group, an indazole group, a purine group,a quinoline group, an isoquinoline group, a benzoquinoline group, aphthalazine group, a naphthyridine group, a quinoxaline group, aquinazoline group, a cinnoline group, a phenanthridine group, anacridine group, a phenanthroline group, a phenazine group, abenzimidazole group, an isobenzothiazole group, a benzoxazole group, anisobenzoxazole group, a triazole group, a tetrazole group, an oxadiazolegroup, a triazine group, a thiadiazole group, an imidazopyridine group,an imidazopyrimidine group, and an azacarbazole group; and

a benzene group, a naphthalene group, a fluorene group, aspiro-bifluorene group, a benzofluorene group, a dibenzofluorene group,a phenalene group, a phenanthrene group, an anthracene group, afluoranthene group, a triphenylene group, a pyrene group, a chrysenegroup, a naphthacene group, a picene group, a perylene group, apentaphene group, an indenoanthracene group, a dibenzofuran group, adibenzothiophene group, a carbazole group, an imidazole group, apyrazole group, a thiazole group, an isothiazole group, an oxazolegroup, an isoxazole group, a pyridine group, a pyrazine group, apyrimidine group, a pyridazine group, an indazole group, a purine group,a quinoline group, an isoquinoline group, a benzoquinoline group, aphthalazine group, a naphthyridine group, a quinoxaline group, aquinazoline group, a cinnoline group, a phenanthridine group, anacridine group, a phenanthroline group, a phenazine group, abenzimidazole group, an isobenzothiazole group, a benzoxazole group, anisobenzoxazole group, a triazole group, a tetrazole group, an oxadiazolegroup, a triazine group, a thiadiazole group, an imidazopyridine group,an imidazopyrimidine group, and an azacarbazole group, each substitutedwith at least one selected from deuterium, —F, —Cl, —Br, —I, a hydroxylgroup, a cyano group, a nitro group, an amidino group, a hydrazinogroup, a hydrazono group, a C₁-C₂₀ alkyl group, a C₁-C₂₀ alkoxy group, aphenyl group, a biphenyl group, a terphenyl group, a naphthyl group,—Si(Q₃₁)(Q₃₂)(Q₃₃), —S(═O)₂(Q₃₁), and —P(═O)(Q₃₁)(Q₃₂), and

Q₃₁ to Q₃₃ may each independently be selected from a C₁-C₁₀ alkyl group,a C₁-C₁₀ alkoxy group, a phenyl group, a biphenyl group, a terphenylgroup, and a naphthyl group.

When xe11 in Formula 601 is two or more, two or more Ar601(s) may belinked via a single bond.

In one or more embodiments, Ar₆₀₁ in Formula 601 may be an anthracenegroup.

In one or more embodiments, the compound represented by Formula 601 maybe represented by Formula 601-1:

In Formula 601-1,

X₆₁₄ may be N or C(R₆₁₄), X₆₁₅ may be N or C(R₆₁₅), X₆₁₆ may be N orC(R₆₁₆), and at least one selected from X₆₁₄ to X₆₁₆ may be N,

L₆₁₁ to L₆₁₃ may each independently be the same as defined in connectionwith L₆₀₁,

xe611 to xe613 may each independently be the same as defined inconnection with xe1,

R₆₁₁ to R₆₁₃ may each independently be the same as defined in connectionwith R₆₀₁, and

R₆₁₄ to R₆₁₆ may each independently be selected from hydrogen,deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitrogroup, an amidino group, a hydrazino group, a hydrazono group, a C₁-C₂₀alkyl group, a C₁-C₂₀ alkoxy group, a phenyl group, a biphenyl group, aterphenyl group, and a naphthyl group.

In one embodiment, in Formulae 601 and 601-1, L₆₀₁ and L₆₁₁ to L₆₁₃ mayeach independently be selected from:

a phenylene group, a naphthylene group, a fluorenylene group, aspiro-bifluorenylene group, a benzofluorenylene group, adibenzofluorenylene group, a phenanthrenylene group, an anthracenylenegroup, a fluoranthenylene group, a triphenylenylene group, a pyrenylenegroup, a chrysenylene group, a perylenylene group, a pentaphenylenegroup, a hexacenylene group, a pentacenylene group, a thiophenylenegroup, a furanylene group, a carbazolylene group, an indolylene group,an isoindolylene group, a benzofuranylene group, a benzothiophenylenegroup, a dibenzofuranylene group, a dibenzothiophenylene group, abenzocarbazolylene group, a dibenzocarbazolylene group, adibenzosilolylene group, a pyridinylene group, an imidazolylene group, apyrazolylene group, a thiazolylene group, an isothiazolylene group, anoxazolylene group, an isoxazolylene group, a thiadiazolylene group, anoxadiazolylene group, a pyrazinylene group, a pyrimidinylene group, apyridazinylene group, a triazinylene group, a quinolinylene group, anisoquinolinylene group, a benzoquinolinylene group, a phthalazinylenegroup, a naphthyridinylene group, a quinoxalinylene group, aquinazolinylene group, a cinnolinylene group, a phenanthridinylenegroup, an acridinylene group, a phenanthrolinylene group, aphenazinylene group, a benzimidazolylene group, an isobenzothiazolylenegroup, a benzoxazolylene group, an isobenzoxazolylene group, atriazolylene group, a tetrazolylene group, an imidazopyridinylene group,an imidazopyrimidinylene group, and an azacarbazolylene group; and

a phenylene group, a naphthylene group, a fluorenylene group, aspiro-bifluorenylene group, a benzofluorenylene group, adibenzofluorenylene group, a phenanthrenylene group, an anthracenylenegroup, a fluoranthenylene group, a triphenylenylene group, a pyrenylenegroup, a chrysenylene group, a perylenylene group, a pentaphenylenegroup, a hexacenylene group, a pentacenylene group, a thiophenylenegroup, a furanylene group, a carbazolylene group, an indolylene group,an isoindolylene group, a benzofuranylene group, a benzothiophenylenegroup, a dibenzofuranylene group, a dibenzothiophenylene group, abenzocarbazolylene group, a dibenzocarbazolylene group, adibenzosilolylene group, a pyridinylene group, an imidazolylene group, apyrazolylene group, a thiazolylene group, an isothiazolylene group, anoxazolylene group, an isoxazolylene group, a thiadiazolylene group, anoxadiazolylene group, a pyrazinylene group, a pyrimidinylene group, apyridazinylene group, a triazinylene group, a quinolinylene group, anisoquinolinylene group, a benzoquinolinylene group, a phthalazinylenegroup, a naphthyridinylene group, a quinoxalinylene group, aquinazolinylene group, a cinnolinylene group, a phenanthridinylenegroup, an acridinylene group, a phenanthrolinylene group, aphenazinylene group, a benzimidazolylene group, an isobenzothiazolylenegroup, a benzoxazolylene group, an isobenzoxazolylene group, atriazolylene group, a tetrazolylene group, an imidazopyridinylene group,an imidazopyrimidinylene group, and an azacarbazolylene group, eachsubstituted with at least one selected from deuterium, —F, —Cl, —Br, —I,a hydroxyl group, a cyano group, a nitro group, an amidino group, ahydrazino group, a hydrazono group, a C₁-C₂₀ alkyl group, a C₁-C₂₀alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, anaphthyl group, a fluorenyl group, a spiro-bifluorenyl group, abenzofluorenyl group, a dibenzofluorenyl group, a phenanthrenyl group,an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, apyrenyl group, a chrysenyl group, a perylenyl group, a pentaphenylgroup, a hexacenyl group, a pentacenyl group, a thiophenyl group, afuranyl group, a carbazolyl group, an indolyl group, an isoindolylgroup, a benzofuranyl group, a benzothiophenyl group, a dibenzofuranylgroup, a dibenzothiophenyl group, a benzocarbazolyl group, adibenzocarbazolyl group, a dibenzosilolyl group, a pyridinyl group, animidazolyl group, a pyrazolyl group, a thiazolyl group, an isothiazolylgroup, an oxazolyl group, an isoxazolyl group, a thiadiazolyl group, anoxadiazolyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinylgroup, a triazinyl group, a quinolinyl group, an isoquinolinyl group, abenzoquinolinyl group, a phthalazinyl group, a naphthyridinyl group, aquinoxalinyl group, a quinazolinyl group, a cinnolinyl group, aphenanthridinyl group, an acridinyl group, a phenanthrolinyl group, aphenazinyl group, a benzimidazolyl group, an isobenzothiazolyl group, abenzoxazolyl group, an isobenzoxazolyl group, a triazolyl group, atetrazolyl group, an imidazopyridinyl group, an imidazopyrimidinylgroup, and an azacarbazolyl group,

but embodiments of the present disclosure are not limited thereto.

In one or more embodiments, in Formulae 601 and 601-1, xe1 and xe611 toxe613 may each independently be 0, 1, or 2.

In one or more embodiments, in Formulae 601 and 601-1, R₆₀₁ and R₆₁₁ toR₆₁₃ may each independently be selected from:

a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, afluorenyl group, a spiro-bifluorenyl group, a benzofluorenyl group, adibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, afluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenylgroup, a perylenyl group, a pentaphenyl group, a hexacenyl group, apentacenyl group, a thiophenyl group, a furanyl group, a carbazolylgroup, an indolyl group, an isoindolyl group, a benzofuranyl group, abenzothiophenyl group, a dibenzofuranyl group, a dibenzothiophenylgroup, a benzocarbazolyl group, a dibenzocarbazolyl group, adibenzosilolyl group, a pyridinyl group, an imidazolyl group, apyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolylgroup, an isoxazolyl group, a thiadiazolyl group, an oxadiazolyl group,a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a triazinylgroup, a quinolinyl group, an isoquinolinyl group, a benzoquinolinylgroup, a phthalazinyl group, a naphthyridinyl group, a quinoxalinylgroup, a quinazolinyl group, a cinnolinyl group, a phenanthridinylgroup, an acridinyl group, a phenanthrolinyl group, a phenazinyl group,a benzimidazolyl group, an isobenzothiazolyl group, a benzoxazolylgroup, an isobenzoxazolyl group, a triazolyl group, a tetrazolyl group,an imidazopyridinyl group, an imidazopyrimidinyl group, and anazacarbazolyl group;

a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, afluorenyl group, a spiro-bifluorenyl group, a benzofluorenyl group, adibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, afluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenylgroup, a perylenyl group, a pentaphenyl group, a hexacenyl group, apentacenyl group, a thiophenyl group, a furanyl group, a carbazolylgroup, an indolyl group, an isoindolyl group, a benzofuranyl group, abenzothiophenyl group, a dibenzofuranyl group, a dibenzothiophenylgroup, a benzocarbazolyl group, a dibenzocarbazolyl group, adibenzosilolyl group, a pyridinyl group, an imidazolyl group, apyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolylgroup, an isoxazolyl group, a thiadiazolyl group, an oxadiazolyl group,a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a triazinylgroup, a quinolinyl group, an isoquinolinyl group, a benzoquinolinylgroup, a phthalazinyl group, a naphthyridinyl group, a quinoxalinylgroup, a quinazolinyl group, a cinnolinyl group, a phenanthridinylgroup, an acridinyl group, a phenanthrolinyl group, a phenazinyl group,a benzimidazolyl group, an isobenzothiazolyl group, a benzoxazolylgroup, an isobenzoxazolyl group, a triazolyl group, a tetrazolyl group,an imidazopyridinyl group, an imidazopyrimidinyl group, and anazacarbazolyl group, each substituted with at least one selected fromdeuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitrogroup, an amidino group, a hydrazino group, a hydrazono group, a C₁-C₂₀alkyl group, a C₁-C₂₀ alkoxy group, a phenyl group, a biphenyl group, aterphenyl group, a naphthyl group, a fluorenyl group, aspiro-bifluorenyl group, a benzofluorenyl group, a dibenzofluorenylgroup, a phenanthrenyl group, an anthracenyl group, a fluoranthenylgroup, a triphenylenyl group, a pyrenyl group, a chrysenyl group, aperylenyl group, a pentaphenyl group, a hexacenyl group, a pentacenylgroup, a thiophenyl group, a furanyl group, a carbazolyl group, anindolyl group, an isoindolyl group, a benzofuranyl group, abenzothiophenyl group, a dibenzofuranyl group, a dibenzothiophenylgroup, a benzocarbazolyl group, a dibenzocarbazolyl group, adibenzosilolyl group, a pyridinyl group, an imidazolyl group, apyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolylgroup, an isoxazolyl group, a thiadiazolyl group, an oxadiazolyl group,a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a triazinylgroup, a quinolinyl group, an isoquinolinyl group, a benzoquinolinylgroup, a phthalazinyl group, a naphthyridinyl group, a quinoxalinylgroup, a quinazolinyl group, a cinnolinyl group, a phenanthridinylgroup, an acridinyl group, a phenanthrolinyl group, a phenazinyl group,a benzimidazolyl group, an isobenzothiazolyl group, a benzoxazolylgroup, an isobenzoxazolyl group, a triazolyl group, a tetrazolyl group,an imidazopyridinyl group, an imidazopyrimidinyl group, and anazacarbazolyl group; and

—S(═O)₂(Q₆₀₁) and —P(═O)(Q₆₀₁)(Q₆₀₂), and

Q₆₀₁ and Q₆₀₂ are the same as described herein above.

The electron transport region may include at least one compound selectedfrom Compounds ET1 to ET36, but embodiments of the present disclosureare not limited thereto:

In one embodiment, the electron transport region may include at leastone compound selected from 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline(BCP), 4,7-diphenyl-1,10-phenanthroline (Bphen), Alq₃, BAlq,3-(biphenyl-4-yl)-5-(4-tert-butylphenyl)-4-phenyl-4H-1,2,4-triazole(TAZ), NTAZ, diphenyl(4-(triphenylsilyl)phenyl)-phosphine oxide (TSPO1),and 3P-T2T:

A thickness of the buffer layer, the hole blocking layer, or theelectron control layer may be in a range of about 20 Å to about 1,000 Å,for example, about 30 Å to about 300 Å. When the thicknesses of thebuffer layer, the hole blocking layer, and the electron control layerare within these ranges, the electron blocking layer may have excellentelectron blocking characteristics or electron control characteristicswithout a substantial increase in driving voltage.

A thickness of the electron transport layer may be in a range of about100 Å to about 1,000 Å, for example, about 150 Å to about 500 Å. Whenthe thickness of the electron transport layer is within the rangedescribed above, the electron transport layer may have suitable orsatisfactory electron transport characteristics without a substantialincrease in driving voltage.

The electron transport region (for example, the electron transport layerin the electron transport region) may further include, in addition tothe materials described above, a metal-containing material.

The metal-containing material may include at least one selected fromalkali metal complex and alkaline earth-metal complex. The alkali metalcomplex may include a metal ion selected from a Li ion, a Na ion, a Kion, a Rb ion, and a Cs ion, and the alkaline earth-metal complex mayinclude a metal ion selected from a Be ion, a Mg ion, a Ca ion, a Srion, and a Ba ion. A ligand coordinated with the metal ion of the alkalimetal complex or the alkaline earth-metal complex may be selected from ahydroxy quinoline, a hydroxy isoquinoline, a hydroxy benzoquinoline, ahydroxy acridine, a hydroxy phenanthridine, a hydroxy phenyloxazolegroup, a hydroxy phenylthiazole group, a hydroxy diphenyloxadiazolegroup, a hydroxy diphenylthiadiazol, a hydroxy phenylpyridine, a hydroxyphenylbenzimidazole group, a hydroxy phenylbenzothiazole group, abipyridine, a phenanthroline, and a cyclopentadiene, but embodiments ofthe present disclosure are not limited thereto.

For example, the metal-containing material may include a Li complex. TheLi complex may include, for example, Compound ET-D1 (lithium quinolate,LiQ) or ET-D2.

The electron transport region may include an electron injection layerthat facilitates injection of electrons from the second electrode 190.The electron injection layer may directly contact the second electrode190.

The electron injection layer may have i) a single-layered structureincluding a single layer including a single material, ii) asingle-layered structure including a single layer including a pluralityof different materials, or iii) a multi-layered structure having aplurality of layers including a plurality of different materials.

The electron injection layer may include an alkali metal, an alkalineearth metal, a rare earth metal, an alkali metal compound, an alkalineearth-metal compound, a rare earth metal compound, an alkali metalcomplex, an alkaline earth-metal complex, a rare earth metal complex, orany combinations thereof.

The alkali metal may be selected from Li, Na, K, Rb, and Cs. In oneembodiment, the alkali metal may be Li, Na, or Cs. In one or moreembodiments, the alkali metal may be Li or Cs, but embodiments of thepresent disclosure are not limited thereto.

The alkaline earth metal may be selected from Mg, Ca, Sr, and Ba.

The rare earth metal may be selected from Sc, Y, Ce, Tb, Yb, and Gd.

The alkali metal compound, the alkaline earth-metal compound, and therare earth metal compound may be selected from oxides and halides (forexample, fluorides, chlorides, bromides, or iodides) of the alkalimetal, the alkaline earth-metal, and the rare earth metal.

The alkali metal compound may be selected from alkali metal oxides, suchas Li₂O, Cs₂O, or K₂O, and alkali metal halides, such as LiF, NaF, CsF,KF, LiI, NaI, CsI, or KI. In one embodiment, the alkali metal compoundmay be selected from LiF, Li₂O, NaF, LiI, NaI, CsI, and KI, butembodiments of the present disclosure are not limited thereto.

The alkaline earth-metal compound may be selected from alkalineearth-metal oxides, such as BaO, SrO, CaO, Ba_(x)Sr_(1-x)O (0<x<1),Ba_(x)Ca_(1-x)O (0<x<1). In one embodiment, the alkaline earth-metalcompound may be selected from BaO, SrO, and CaO, but embodiments of thepresent disclosure are not limited thereto.

The rare earth metal compound may be selected from YbF₃, ScF₃, ScO₃,Y₂O₃, Ce₂O₃, GdF₃, and TbF₃. In one embodiment, the rare earth metalcompound may be selected from YbF₃, ScF₃, TbF₃, YbI₃, ScI₃, and TbI₃,but embodiments of the present disclosure are not limited thereto.

The alkali metal complex, the alkaline earth-metal complex, and the rareearth metal complex may include an ion of alkali metal, alkalineearth-metal, and rare earth metal as described above, and a ligandcoordinated with a metal ion of the alkali metal complex, the alkalineearth-metal complex, or the rare earth metal complex may be selectedfrom hydroxy quinoline, hydroxy isoquinoline, hydroxy benzoquinoline,hydroxy acridine, hydroxy phenanthridine, hydroxy phenyloxazole, hydroxyphenylthiazole, hydroxy diphenyloxadiazole, hydroxy diphenylthiadiazol,hydroxy phenylpyridine, hydroxy phenylbenzimidazole, hydroxyphenylbenzothiazole, bipyridine, phenanthroline, and cyclopentadiene,but embodiments of the present disclosure are not limited thereto.

The electron injection layer may consist of an alkali metal, an alkalineearth metal, a rare earth metal, an alkali metal compound, an alkalineearth-metal compound, a rare earth metal compound, an alkali metalcomplex, an alkaline earth-metal complex, a rare earth metal complex, orany combinations thereof, as described above. In one or moreembodiments, the electron injection layer may further include an organicmaterial. When the electron injection layer further includes an organicmaterial, an alkali metal, an alkaline earth metal, a rare earth metal,an alkali metal compound, an alkaline earth-metal compound, a rare earthmetal compound, an alkali metal complex, an alkaline earth-metalcomplex, a rare earth metal complex, or any combinations thereof may behomogeneously or non-homogeneously dispersed in a matrix including theorganic material.

A thickness of the electron injection layer may be in a range of about 1Å to about 100 Å, for example, about 3 Å to about 90 Å. When thethickness of the electron injection layer is within the range describedabove, the electron injection layer may have suitable or satisfactoryelectron injection characteristics without a substantial increase indriving voltage.

Second Electrode 190

The second electrode 190 may be on the organic layer 150 having such astructure. The second electrode 190 may be a cathode which is anelectron injection electrode, and in this regard, a material for formingthe second electrode 190 may be selected from metal, an alloy, anelectrically conductive compound, and a combination thereof, which havea relatively low work function.

The second electrode 190 may include at least one selected from lithium(Li), silver (Ag), magnesium (Mg), aluminum (Al), aluminum-lithium(Al—Li), calcium (Ca), magnesium-indium (Mg—In), magnesium-silver(Mg—Ag), ITO, and IZO, but embodiments of the present disclosure are notlimited thereto. The second electrode 190 may be a transmissiveelectrode, a semi-transmissive electrode, or a reflective electrode.

The second electrode 190 may have a single-layered structure, or amulti-layered structure including two or more layers.

Description of FIGS. 2 to 4

An organic light-emitting device 20 of FIG. 2 includes a first cappinglayer 210, a first electrode 110, an organic layer 150, and a secondelectrode 190 which are sequentially stacked in this stated order, anorganic light-emitting device 30 of FIG. 3 includes a first electrode110, an organic layer 150, a second electrode 190, and a second cappinglayer 220 which are sequentially stacked in this stated order, and anorganic light-emitting device 40 of FIG. 4 includes a first cappinglayer 210, a first electrode 110, an organic layer 150, a secondelectrode 190, and a second capping layer 220.

Regarding FIGS. 2 to 4, the first electrode 110, the organic layer 150,and the second electrode 190 may be understood by referring to thedescription presented in connection with FIG. 1.

In the organic layer 150 of each of the organic light-emitting devices20 and 40, light generated in an emission layer may pass through thefirst electrode 110, which is a semi-transmissive electrode or atransmissive electrode, and the first capping layer 210 toward theoutside, and in the organic layer 150 of each of the organiclight-emitting devices 30 and 40, light generated in an emission layermay pass through the second electrode 190, which is a semi-transmissiveelectrode or a transmissive electrode, and the second capping layer 220toward the outside.

The first capping layer 210 and the second capping layer 220 mayincrease external luminescent efficiency according to the principle ofconstructive interference.

The first capping layer 210 and the second capping layer 220 may eachindependently be an organic capping layer including an organic material,an inorganic capping layer including an inorganic material, or acomposite capping layer including an organic material and an inorganicmaterial.

At least one selected from the first capping layer 210 and the secondcapping layer 220 may each independently include at least one materialselected from carbocyclic compounds, heterocyclic compounds, amine-basedcompounds, porphyrine derivatives, phthalocyanine derivatives, anaphthalocyanine derivatives, alkali metal complexes, and alkalineearth-based complexes. The carbocyclic compound, the heterocycliccompound, and the amine-based compound may be optionally substitutedwith a substituent containing at least one element selected from O, N,S, Se, Si, F, Cl, Br, and I. In one embodiment, at least one selectedfrom the first capping layer 210 and the second capping layer 220 mayeach independently include an amine-based compound.

In one embodiment, at least one selected from the first capping layer210 and the second capping layer 220 may each independently include thecompound represented by Formula 201 or the compound represented byFormula 202.

In one or more embodiments, at least one selected from the first cappinglayer 210 and the second capping layer 220 may each independentlyinclude a compound selected from Compounds HT28 to HT33 and CompoundsCP1 to CP5, but embodiments of the present disclosure are not limitedthereto.

Hereinbefore, the organic light-emitting device according to anembodiment has been described in connection with FIGS. 1 to 4. However,embodiments of the present disclosure are not limited thereto.

Layers constituting the hole transport region, an emission layer, andlayers constituting the electron transport region may be formed in acertain region by using one or more suitable methods selected fromvacuum deposition, spin coating, casting, Langmuir-Blodgett (LB)deposition, ink-jet printing, laser-printing, and laser-induced thermalimaging.

When layers constituting the hole transport region, an emission layer,and layers constituting the electron transport region are formed byvacuum deposition, the deposition may be performed at a depositiontemperature of about 100° C. to about 500° C., a vacuum degree of about10⁻⁸ torr to about 10⁻³ torr, and a deposition speed of about 0.01 Å/secto about 100 Å/sec by taking into account a material to be included in alayer to be formed, and the structure of a layer to be formed.

When layers constituting the hole transport region, an emission layer,and layers constituting the electron transport region are formed by spincoating, the spin coating may be performed at a coating speed of about2000 rpm to about 5000 rpm and at a heat treatment temperature of about80° C. to about 200° C. by taking into account a material to be includedin a layer to be formed, and the structure of a layer to be formed.

Display Apparatus

The organic light-emitting device may be included in a display deviceincluding a thin film transistor. The thin film transistor may include asource electrode, a drain electrode, and an active layer, and one of thesource electrode and the drain electrode may electrically contact afirst electrode of the organic light-emitting device.

The thin film transistor may further include a gate electrode, a gateinsulation layer, and/or the like.

The active layer may include crystalline silicon, amorphous silicon,organic semiconductor, oxide semiconductor, and/or the like, butembodiments of the present disclosure are not limited thereto.

The display apparatus may further include a sealing member that sealsthe organic light-emitting device. The sealing member may enable toimplement an image from the organic light-emitting device, and mayprevent or reduce penetration of external air and moisture into theorganic light-emitting device. The sealing member may be a sealingsubstrate made of glass or plastic. The sealing member may be athin-film encapsulation layer including a plurality of organic layersand/or a plurality of inorganic layers. When sealing member is athin-film encapsulation layer, the whole flat display apparatus may bemade flexible.

General Definition of at Least Some of the Substituents

The term “C₁-C₆₀ alkyl group,” as used herein, refers to a linear orbranched saturated aliphatic hydrocarbon monovalent group having 1 to 60carbon atoms, and examples thereof include a methyl group, an ethylgroup, a propyl group, an isobutyl group, a sec-butyl group, atert-butyl group, a pentyl group, an isoamyl group, and a hexyl group.The term “C₁-C₆₀ alkylene group,” as used herein, refers to a divalentgroup having substantially the same structure as the C₁-C₆₀ alkyl group.

The term “C₂-C₆₀ alkenyl group,” as used herein, refers to a hydrocarbongroup having at least one double bond at a main chain (e.g., in themiddle) or at a terminal end (e.g., at the terminus) of the C₂-C₆₀ alkylgroup, and examples thereof include an ethenyl group, a propenyl group,and a butenyl group. The term “C₂-C₆₀ alkenylene group,” as used herein,refers to a divalent group having substantially the same structure asthe C₂-C₆₀ alkenyl group.

The term “C₂-C₆₀ alkynyl group,” as used herein, refers to a hydrocarbongroup having at least one triple bond at a main chain (e.g., in themiddle) or at a terminal end (e.g., at the terminus) of the C₂-C₆₀ alkylgroup, and examples thereof include an ethynyl group, and a propynylgroup. The term “C₂-C₆₀ alkynylene group,” as used herein, refers to adivalent group having substantially the same structure as the C₂-C₆₀alkynyl group.

The term “C₁-C₆₀ alkoxy group,” as used herein, refers to a monovalentgroup represented by —OA₁₀₁ (wherein A₁₀₁ is the C₁-C₆₀ alkyl group),and examples thereof include a methoxy group, an ethoxy group, and anisopropyloxy group.

The term “C₃-C₁₀ cycloalkyl group,” as used herein, refers to amonovalent saturated hydrocarbon monocyclic group having 3 to 10 carbonatoms, and examples thereof include a cyclopropyl group, a cyclobutylgroup, a cyclopentyl group, a cyclohexyl group, and a cycloheptyl group.The term “C₃-C₁₀ cycloalkylene group,” as used herein, refers to adivalent group having substantially the same structure as the C₃-C₁₀cycloalkyl group.

The term “C₁-C₁₀ heterocycloalkyl group,” as used herein, refers to amonovalent monocyclic group having at least one heteroatom selected fromN, O, Si, P, and S as a ring-forming atom and 1 to 10 carbon atoms, andexamples thereof include a 1,2,3,4-oxatriazolidinyl group, atetrahydrofuranyl group, and a tetrahydrothiophenyl group. The term“C₁-C₁₀ heterocycloalkylene group,” as used herein, refers to a divalentgroup having substantially the same structure as the C₁-C₁₀heterocycloalkyl group.

The term “C₃-C₁₀ cycloalkenyl group,” as used herein, refers to amonovalent monocyclic group that has 3 to 10 carbon atoms and at leastone double bond in the ring thereof and no aromaticity (e.g., the entirering and/or group is not aromatic), and examples thereof include acyclopentenyl group, a cyclohexenyl group, and a cycloheptenyl group.The term “C₃-C₁₀ cycloalkenylene group,” as used herein, refers to adivalent group having substantially the same structure as the C₃-C₁₀cycloalkenyl group.

The term “C₁-C₁₀ heterocycloalkenyl group,” as used herein, refers to amonovalent monocyclic group that has at least one heteroatom selectedfrom N, O, Si, P, and S as a ring-forming atom, 1 to 10 carbon atoms,and at least one double bond in its ring. Non-limiting examples of theC₁-C₁₀ heterocycloalkenyl group include a4,5-dihydro-1,2,3,4-oxatriazolyl group, a 2,3-dihydrofuranyl group, anda 2,3-dihydrothiophenyl group. The term “C₁-C₁₀ heterocycloalkenylenegroup,” as used herein, refers to a divalent group having substantiallythe same structure as the C₁-C₁₀ heterocycloalkenyl group.

The term “C₆-C₆₀ aryl group,” as used herein, refers to a monovalentgroup having a carbocyclic aromatic system having 6 to 60 carbon atoms,and a C₆-C₆₀ arylene group used herein refers to a divalent group havinga carbocyclic aromatic system having 6 to 60 carbon atoms. Examples ofthe C₆-C₆₀ aryl group are a phenyl group, a naphthyl group, ananthracenyl group, a phenanthrenyl group, a pyrenyl group, and achrysenyl group. When the C₆-C₆₀ aryl group and the C₆-C₆₀ arylene groupeach include two or more rings, the rings may be fused to each other(e.g., combined together).

The term “C₁-C₆₀ heteroaryl group,” as used herein, refers to amonovalent group having a carbocyclic aromatic system that has at leastone heteroatom selected from N, O, Si, P, and S as a ring-forming atom,in addition to 1 to 1 carbon atoms. The term “C₁-C₆₀ heteroarylenegroup,” as used herein, refers to a divalent group having a carbocyclicaromatic system that has at least one heteroatom selected from N, O, Si,P, and S as a ring-forming atom, in addition to 1 to 60 carbon atoms.Examples of the C₁-C₆₀ heteroaryl group are a pyridinyl group, apyrimidinyl group, a pyrazinyl group, a pyridazinyl group, a triazinylgroup, a quinolinyl group, and an isoquinolinyl group. When the C₁-C₆₀heteroaryl group and the C₁-C₆₀ heteroarylene group each include two ormore rings, the rings may be fused to each other (e.g., combinedtogether).

The term “C₆-C₆₀ aryloxy group,” as used herein, indicates —OA₁₀₂(wherein A₁₀₂ is the C₆-C₆₀ aryl group), and a C₆-C₆₀ arylthio groupindicates —SA₁₀₃ (wherein A₁₀₃ is the C₆-C₆₀ aryl group).

The term “C₁-C₆₀ heteroaryloxy group,” as used herein, indicates —OA₁₀₄(wherein A₁₀₄ is the C₁-C₆₀ heteroaryl group), and the term “C6-C₆₀heteroarylthio group,” as used herein, indicates —SA105 (wherein A₁₀₅ isthe C₁-C₆₀ heteroaryl group).

The term “monovalent non-aromatic condensed polycyclic group,” as usedherein, refers to a monovalent group (for example, having 8 to 60 carbonatoms) having two or more rings condensed with each other (e.g.,combined together), only carbon atoms as ring-forming atoms, and noaromaticity in its entire molecular structure (e.g., the entire groupand/or molecule is not aromatic). An example of the monovalentnon-aromatic condensed polycyclic group is a fluorenyl group. The term“divalent non-aromatic condensed polycyclic group,” as used herein,refers to a divalent group having substantially the same structure asthe monovalent non-aromatic condensed polycyclic group.

The term “monovalent non-aromatic condensed heteropolycyclic group,” asused herein, refers to a monovalent group (for example, having 1 to 60carbon atoms) having two or more rings condensed to each other (e.g.,combined together), at least one heteroatom selected from N, O, Si, P,and S, other than carbon atoms, as a ring-forming atom, and noaromaticity in its entire molecular structure (e.g., the entire groupand/or molecule is not aromatic). An example of the monovalentnon-aromatic condensed heteropolycyclic group is a carbazolyl group. Theterm “divalent non-aromatic condensed heteropolycyclic group,” as usedherein, refers to a divalent group having substantially the samestructure as the monovalent non-aromatic condensed heteropolycyclicgroup.

The term “C₅-C₆₀ carbocyclic group,” as used herein, refers to amonocyclic or polycyclic group having 5 to 60 carbon atoms in which aring-forming atom is a carbon atom only. The C₅-C₆₀ carbocyclic groupmay be an aromatic carbocyclic group or a non-aromatic carbocyclicgroup. The C₅-C₆₀ carbocyclic group may be a ring, such as benzene, amonovalent group, such as a phenyl group, or a divalent group, such as aphenylene group. In one or more embodiments, depending on the number ofsubstituents connected to the C₅-C₆₀ carbocyclic group, the C₅-C₆₀carbocyclic group may be a trivalent group or a quadrivalent group.

The term “C₁-C₆₀ heterocyclic group,” as used herein, refers to a grouphaving substantially the same structure as the C₅-C₆₀ carbocyclic group,except that as a ring-forming atom, at least one heteroatom selectedfrom N, O, Si, P, and S is used in addition to carbon (the number ofcarbon atoms may be in a range of 1 to 60).

In the specification, at least one substituent of the substituted C₅-C₆₀carbocyclic group, the substituted C₁-C₆₀ heterocyclic group, thesubstituted C₃-C₁₀ cycloalkylene group, the substituted C₁-C₁₀heterocycloalkylene group, the substituted C₃-C₁₀ cycloalkenylene group,the substituted C₁-C₁₀ heterocycloalkenylene group, the substitutedC₆-C₆₀ arylene group, the substituted C₁-C₆₀ heteroarylene group, thesubstituted divalent non-aromatic condensed polycyclic group, thesubstituted divalent non-aromatic condensed heteropolycyclic group, thesubstituted C₁-C₆₀ alkyl group, the substituted C₂-C₆₀ alkenyl group,the substituted C₂-C₆₀ alkynyl group, the substituted C₁-C₆₀ alkoxygroup, the substituted C₃-C₁₀ cycloalkyl group, the substituted C₁-C₁₀heterocycloalkyl group, the substituted C₃-C₁₀ cycloalkenyl group, thesubstituted C₁-C₁₀ heterocycloalkenyl group, the substituted C₆-C₆₀ arylgroup, the substituted C₆-C₆₀ aryloxy group, the substituted C₆-C₆₀arylthio group, the substituted C₁-C₆₀ heteroaryl group, the substitutedC₁-C₆₀ heteroaryloxy group, the substituted C₁-C₆₀ heteroarylthio group,the substituted monovalent non-aromatic condensed polycyclic group, andthe substituted monovalent non-aromatic condensed heteropolycyclic groupmay be selected from:

deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitrogroup, an amidino group, a hydrazino group, a hydrazono group, a C₁-C₆₀alkyl group, a C₂-C₆₀ alkenyl group, a C₂-C₆₀ alkynyl group, and aC₁-C₆₀ alkoxy group;

a C₁-C₆₀ alkyl group, a C₂-C₆₀ alkenyl group, a C₂-C₆₀ alkynyl group,and a C₁-C₆₀ alkoxy group, each substituted with at least one selectedfrom deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, anitro group, an amidino group, a hydrazino group, a hydrazono group, aC₃-C₁₀ cycloalkyl group, a C₁-C₁₀ heterocycloalkyl group, a C₃-C₁₀cycloalkenyl group, a C₁-C₁₀ heterocycloalkenyl group, a C₆-C₆₀ arylgroup, a C₆-C₆₀ aryloxy group, a C₆-C₆₀ arylthio group, a C₁-C₆₀heteroaryl group, a C₁-C₆₀ heteroaryloxy group, a C₁-C₆₀ heteroarylthiogroup, a monovalent non-aromatic condensed polycyclic group, amonovalent non-aromatic condensed heteropolycyclic group,—Si(Q₁₁)(Q₁₂)(Q₁₃), —N(Q₁₁)(Q₁₂), —B(Q₁₁)(Q₁₂), —C(═O)(Q₁₁),—S(═O)₂(Q₁₁), and —P(═O)(Q₁₁)(Q₁₂);

a C₃-C₁₀ cycloalkyl group, a C₁-C₁₀ heterocycloalkyl group, a C₃-C₁₀cycloalkenyl group, a C₁-C₁₀ heterocycloalkenyl group, a C₆-C₆₀ arylgroup, a C₆-C₆₀ aryloxy group, a C₆-C₆₀ arylthio group, a C₁-C₆₀heteroaryl group, a C₁-C₆₀ heteroaryloxy group, a C₁-C₆₀ heteroarylthiogroup, a monovalent non-aromatic condensed polycyclic group, and amonovalent non-aromatic condensed heteropolycyclic group;

a C₃-C₁₀ cycloalkyl group, a C₁-C₁₀ heterocycloalkyl group, a C₃-C₁₀cycloalkenyl group, a C₁-C₁₀ heterocycloalkenyl group, a C₆-C₆₀ arylgroup, a C₆-C₆₀ aryloxy group, a C₆-C₆₀ arylthio group, a C₁-C₆₀heteroaryl group, a C₁-C₆₀ heteroaryloxy group, a C₁-C₆₀ heteroarylthiogroup, a monovalent non-aromatic condensed polycyclic group, and amonovalent non-aromatic condensed heteropolycyclic group, eachsubstituted with at least one selected from deuterium, —F, —Cl, —Br, —I,a hydroxyl group, a cyano group, a nitro group, an amidino group, ahydrazino group, a hydrazono group, a C₁-C₆₀ alkyl group, a C₂-C₆₀alkenyl group, a C₂-C₆₀ alkynyl group, a C₁-C₆₀ alkoxy group, a C₃-C₁₀cycloalkyl group, a C₁-C₁₀ heterocycloalkyl group, a C₃-C₁₀ cycloalkenylgroup, a C₁-C₁₀ heterocycloalkenyl group, a C₆-C₆₀ aryl group, a C₆-C₆₀aryloxy group, a C₆-C₆₀ arylthio group, a C₁-C₆₀ heteroaryl group, aC₁-C₆₀ heteroaryloxy group, a C₁-C₆₀ heteroarylthio group, a monovalentnon-aromatic condensed polycyclic group, a monovalent non-aromaticcondensed heteropolycyclic group, —Si(Q₂₁)(Q₂₂)(Q₂₃), —N(Q₂₁)(Q₂₂),—B(Q₂₁)(Q₂₂), —C(═O)(Q₂₁), —S(═O)₂(Q₂₁), and —P(═O)(Q₂₁)(Q₂₂); and

—Si(Q₃₁)(Q₃₂)(Q₃₃), —N(Q₃₁)(Q₃₂), —B(Q₃₁)(Q₃₂), —C(═O)(Q₃₁),—S(═O)₂(Q₃₁), and —P(═O)(Q₃₁)(Q₃₂), and

Q₁₁ to Q₁₃, Q₂₁ to Q₂₃, and Q₃₁ to Q₃₃ may each independently beselected from hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, acyano group, a nitro group, an amidino group, a hydrazino group, ahydrazono group, a C₁-C₆₀ alkyl group, a C₂-C₆₀ alkenyl group, a C₂-C₆₀alkynyl group, a C₁-C₆₀ alkoxy group, a C₃-C₁₀ cycloalkyl group, aC₁-C₁₀ heterocycloalkyl group, a C₃-C₁₀ cycloalkenyl group, a C₁-C₁₀heterocycloalkenyl group, a C₆-C₆₀ aryl group, a C₁-C₆₀ heteroarylgroup, a C₁-C₆₀ heteroaryloxy group, a C₁-C₆₀ heteroarylthio group, amonovalent non-aromatic condensed polycyclic group, a monovalentnon-aromatic condensed heteropolycyclic group, a C₁-C₆₀ alkyl groupsubstituted with at least one selected from deuterium, —F, and a cyanogroup, a C₆-C₆₀ aryl group substituted with at least one selected fromdeuterium, —F, and a cyano group, a biphenyl group, and a terphenylgroup.

The term “Ph,” as used herein, refers to a phenyl group, the term “Me,”as used herein, refers to a methyl group, the term “Et,” as used herein,refers to an ethyl group, the term “ter-Bu” or “Bu^(t),” as used herein,refers to a tert-butyl group, and the term “OMe,” as used herein, refersto a methoxy group.

The term “biphenyl group,” as used herein, refers to “a phenyl groupsubstituted with a phenyl group.” In other words, the “biphenyl group”is a substituted phenyl group having a C₆-C₆₀ aryl group as asubstituent.

The term “terphenyl group,” as used herein, refers to “a phenyl groupsubstituted with a biphenyl group.” In other words, the “terphenylgroup” is a phenyl group having, as a substituent, a C₆-C₆₀ aryl groupsubstituted with a C₆-C₆₀ aryl group.

* and *′, as used herein, unless defined otherwise, each refer to abinding site to a neighboring atom in a corresponding formula.

Hereinafter, a compound according to embodiments and an organiclight-emitting device according to embodiments will be described in moredetail with reference to Synthesis Examples and Examples. The wording “Bwas used instead of A” used in describing Synthesis Examples refers tothat an identical molar equivalent of B was used in place of A.

EXAMPLES Synthesis Example 1 Synthesis of Compound 1

3 g (0.0067 mol) of7,7,11,11-tetramethyl-9-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-7,11-dihydrobenzo[8,1]indolizino[2,3,4,5,6-defg]acridineand 0.96 g (0.0034 mol) of 1,5-dibromonaphthalene were added to athree-neck flask (100 ml), oxygen was removed therefrom, 3 ml of 2NK₂CO₃ and a mixed solution of toluene/EtOH were added thereto, and theresultant was purged with nitrogen. Then, 0.1 g of a catalyst Pd(pph₃)₄was added thereto and the resultant was stirred at a temperature of 100°C. for 24 hours under reflux. Water was added thereto to terminate thereaction, extraction was performed thereon three times by usingdichloromethane, and a solvent was removed therefrom. Columnchromatography using a solvent of ethyl acetate:n-hexane (1:10) wasperformed on the result obtained therefrom to obtain 2.2 g (84%) ofCompound 1.

H-NMR(CDCl₃): 8.90(2H, d), 8.45(2H, d), 8.37(2H, d), 8.12(2H, d), 7.88(4H, s), 7.70 (2H, t), 7.45 (2H, d), 7.20 (2H, t), 7.08 (2H, t), 6.99(2H, d), 1.70 (24H, t).

Synthesis Example 2 Synthesis of Compound 2

3 g (0.0067 mol) of7,7,11,11-tetramethyl-9-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-7,11-dihydrobenzo[8,1]indolizino[2,3,4,5,6-defg]acridineand 0.96 g (0.0034 mol) of 2,6-dibromonaphthalene were added to athree-neck flask (100 ml), oxygen was removed therefrom, 3 ml of 2NK₂CO₃ and a mixed solution of toluene/EtOH were added thereto, and theresultant was purged with nitrogen. Then, 0.1 g of a catalyst Pd(pph₃)₄was added thereto and the resultant was stirred at a temperature of 100°C. for 24 hours under reflux. Water was added thereto to terminate thereaction, extraction was performed thereon three times by usingdichloromethane, and a solvent was removed therefrom. Columnchromatography using a solvent of ethyl acetate:n-hexane (1:10) wasperformed on the result obtained therefrom to obtain 2.2 g (84%) ofCompound 2.

H-NMR(CDCl₃): 8.90(2H, d), 8.45(2H, d), 8.37(2H, d), 8.12(2H, d), 7.88(4H, s), 7.70 (2H, t), 7.45 (2H, d), 7.20 (2H, t), 7.08 (2H, t), 6.99(2H, d), 1.70 (24H, t).

Synthesis Example 3 Synthesis of Compound 3

3 g (0.0067 mol) of7,7,11,11-tetramethyl-9-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-7,11-dihydrobenzo[8,1]indolizino[2,3,4,5,6-defg]acridineand 2.67 g (0.0067 mol) of9-bromo-7,7,11,11-tetramethyl-7,11-dihydrobenzo[8,1]indolizino[2,3,4,5,6-defg]acridinewere added to a three-neck flask (100 ml), oxygen was removed therefrom,3 ml of 2N K₂CO₃ and a mixed solution of toluene/EtOH were addedthereto, and the resultant was purged with nitrogen. Then, 0.1 g of acatalyst Pd(pph₃)₄ was added thereto and the resultant was stirred at atemperature of 100° C. for 24 hours under reflux. Water was addedthereto to terminate the reaction, extraction was performed thereonthree times by using dichloromethane, and a solvent was removedtherefrom. Column chromatography using a solvent of ethylacetate:n-hexane (1:10) was performed on the result obtained therefromto obtain 3.89 g (90%) of Compound 3.

H-NMR(CDCl₃): 8.45(2H, d), 8.09(2H, d), 7.88 (4H, s), 7.45 (2H, d), 7.20(2H, t), 7.08 (2H, t), 6.99 (2H, d), 1.70 (24H, t).

Synthesis Example 4 Synthesis of Compound 4

3 g (0.0067 mol) of7,7,11,11-tetramethyl-8-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-7,11-dihydrobenzo[8,1]indolizino[2,3,4,5,6-defg]acridineand 2.67 g (0.0067 mol) of8-bromo-7,7,11,11-tetramethyl-7,11-dihydrobenzo[8,1]indolizino[2,3,4,5,6-defg]acridinewere added to a three-neck flask (100 ml), oxygen was removed therefrom,3 ml of 2N K₂CO₃ and a mixed solution of toluene/EtOH were addedthereto, and the resultant was purged with nitrogen. Then, 0.1 g of acatalyst Pd(pph₃)₄ was added thereto and the resultant was stirred at atemperature of 100° C. for 24 hours under reflux. Water was addedthereto to terminate the reaction, extraction was performed thereonthree times by using dichloromethane, and a solvent was removedtherefrom. Column chromatography using a solvent of ethylacetate:n-hexane (1:10) was performed on the result obtained therefromto obtain 3.80 g (88%) of Compound 4.

H-NMR(CDCl₃): 8.45(2H, d), 8.09(2H, d), 7.71 (2H, d), 7.45-7.41 (4H, m),7.24 (2H, t), 7.07 (2H, t), 6.98 (2H, d), 1.69 (24H, t).

Synthesis Example 5 Synthesis of Compound 5

3 g (0.0067 mol) of7,7,11,11-tetramethyl-9-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-7,11-dihydrobenzo[8,1]indolizino[2,3,4,5,6-defg]acridineand 0.80 g (0.0034 mol) of 2,6-dibromobenzene were added to a three-neckflask (100 ml), oxygen was removed therefrom, 3 ml of 2N K₂CO₃ and amixed solution of toluene/EtOH were added thereto, and the resultant waspurged with nitrogen. Then, 0.1 g of a catalyst Pd(pph₃)₄ was addedthereto and the resultant was stirred at a temperature of 100° C. for 24hours under reflux. Water was added thereto to terminate the reaction,extraction was performed thereon three times by using dichloromethane,and a solvent was removed therefrom. Column chromatography using asolvent of ethyl acetate:n-hexane (1:10) was performed on the resultobtained therefrom to obtain 1.96 g (80%) of Compound 5.

H-NMR(CDCl₃): 8.45(2H, d), 8.09(2H, d), 7.84 (4H, s), 7.45 (2H, d), 7.25(6H, m), 7.08 (2H, t), 6.99 (2H, d), 1.70 (24H, t).

Synthesis Example 6 Synthesis of Compound 6

3 g (0.0067 mol) of7,7,11,11-tetramethyl-8-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-7,11-dihydrobenzo[8,1]indolizino[2,3,4,5,6-defg]acridineand 0.80 g (0.0034 mol) of 2,6-dibromobenzen were added to a three-neckflask (100 ml), oxygen was removed therefrom, 3 ml of 2N K₂CO₃ and amixed solution of toluene/EtOH were added thereto, and the resultant waspurged with nitrogen. Then, 0.1 g of a catalyst Pd(pph₃)₄ was addedthereto and the resultant was stirred at a temperature of 100° C. for 24hours under reflux. Water was added thereto to terminate the reaction,extraction was performed thereon three times by using dichloromethane,and a solvent was removed therefrom. Column chromatography using asolvent of ethyl acetate:n-hexane (1:10) was performed on the resultobtained therefrom to obtain 1.89 g (77%) of Compound 6.

H-NMR(CDCl₃): 8.45(2H, d), 8.09(2H, d), 7.71 (2H, d), 7.45-7.41 (4H, m),7.25-7.23 (6H, m), 7.07 (2H, t), 6.98 (2H, d), 1.69 (24H, t).

Evaluation Example 1

The HOMO energy level, LUMO energy level, singlet (S₁) energy level, andtriplet (T₁) energy level of TCTA, Compounds 1, 2, 3, 4, 5, 6, A, and Bwere evaluated according to the methods shown in Table 1, and resultsthereof are shown in Table 2.

TABLE 1 HOMO A voltage-current (V-A) graph of each Compound was energyobtained by using a cyclic voltammetry (CV) (electrolyte: level 0.1MBu₄NClO₄/solvent: CH₂Cl₂/electrode: 3-electrode evaluation system (workelectrode: GC, reference electrode: Ag/AgCl, method auxiliary electrode:Pt)), and a HOMO energy level of each Compound was calculated fromreduction onset of the graph. LUMO Each Compound was diluted at aconcentration of energy 1 × 10⁻⁵M in CHCl₃, an UV absorption spectrumlevel thereof was measured at room temperature by evaluation using aShimadzu UV-350 spectrometer, and a method LUMO energy level thereof wascalculated by using an optical band gap (Eg) from an edge of theabsorption spectrum. S₁ energy A photoluminescence spectrum of a mixtureof toluene level and each Compound (diluted at a concentration ofevaluation 1 × 10⁻⁴M) was measured at room temperature by method using aphotoluminescence measurement device, and an observed peak was analyzedto calculate onset S1 energy level. T₁ energy A mixture of toluene andeach Compound (diluted at a level concentration of 1 × 10⁻⁴M) was loadedinto a quartz evaluation cell, and then, the resultant quartz cell wasloaded method into liquid nitrogen (77K), a photoluminescence spectrumthereof was measured by using a photoluminescence measurement device,and the obtained spectrum was compared with a photoluminescence spectrummeasured at room temperature, and peaks observed only at low temperaturewere analyzed to calculate a T₁ energy level.

TABLE 2 HOMO (eV) LUMO (eV) T₁ (eV) S₁ (eV) 1 −5.4 −2.1 2.4 3.1 2 −5.3−2.2 2.4 3.0 3 −5.3 −1.9 2.4 3.1 4 −5.5 −1.8 3.0 3.2 5 −5.4 −2.1 2.3 3.06 −5.6 −2.0 2.8 3.0 A −5.4 −1.9 2.4 3.2 B −5.4 −1.9 2.6 3.1 TCTA −5.4−2.0 2.8 3.2

Evaluation Example 2

In order to calculate the BDE caused by excitons in the anion state, thestructure of each Compound was optimized using Density Functional Theoryusing the B3LYP hybrid functional and the 6-311G** basis set. After thestructure of each Compound was optimized, the most stable structure wasselected in the anion state, and the energy necessary for decomposingthe structure of the Compound was calculated. The BDEs of TCTA,Compounds 1 to 6, A, and B in the anion state were evaluated, andresults thereof are shown in Table 3.

TABLE 3 BDE (eV) 1 3.9 2 4.07 3 4.10 4 3.88 5 4.22 6 4.13 A 4.0 B 3.89TCTA 1.4

From Table 3, it can be seen that Compounds 1 to 6 have relatively veryhigh BDE. For example, it can be seen that Compounds 1 to 6 have muchhigher BDE than TCTA.

Evaluation Example 3

As an anode, HAT-CN was laminated on 800 Å ITO to a thickness of 50 Å,Compounds of Table 4 were deposited to a thickness of 500 Å, HAT-CN waslaminated to a thickness of 50 Å, Ag was deposited to a thickness of 50Å, and AgMg was deposited to a thickness of 1,000 Å, thereby completingthe manufacture of a hole only device (HOD). A position having a slopeof 2 was found by log-plotting y axis, an SCLC region was confirmed, anda mobility was extracted through Equation 1 (Mott-Gurney theoryequation). Results thereof are shown in Table 4.

$\begin{matrix}{J = {\left( \frac{9}{8} \right)ɛ_{r}ɛ_{0}{{\mu_{eff}\left( \frac{V^{2}}{L^{3}} \right)}.}}} & {{Equation}\mspace{14mu} 1}\end{matrix}$

In Equation 1,

V is an applied voltage, and

L is a thickness.

TABLE 4 Hole movement (cm²/Vs) 1 1.5e⁻⁴ 2 9.1e⁻⁵ 3 4.3e⁻⁴ 4 1.2e⁻⁴ 58.5e⁻⁴ 6 7.3e⁻⁴ A 1.2e⁻⁵ B 2.3e⁻⁵ TCTA 3.5e⁻⁴

From Table 4, it is confirmed that Compounds 1 to 6 have very improvedhole movement, as compared with Compounds A and B.

Example 1

As an anode, an ITO substrate, on which ITO/Ag/ITO were deposited, wascut to a size of 50 mm×50 mm×0.7 mm, sonicated with isopropyl alcoholand pure water each for 5 minutes, and then cleaned by exposure toultraviolet rays and ozone for 30 minutes. Then, the ITO substrate wasprovided to a vacuum deposition apparatus.

Compound HAT-CN was vacuum-deposited on the ITO substrate to form a holeinjection layer having a thickness of 5 nm, Compound NPB wasvacuum-deposited on the hole injection layer to form a hole transportlayer having a thickness of 60 nm, and Compound 1 was vacuum-depositedon the hole transport layer to form an electron blocking layer having athickness of 5 nm, and Compound ADN and BCzVBi were co-deposited on theelectron blocking layer at a weight ratio of 97:3 to form an emissionlayer having a thickness of 20 nm. Compound 3P-T2T was deposited on theemission layer to form an electron transport layer having a thickness of30 nm. LiQ was deposited on the electron transport layer to form anelectron injection layer having a thickness of 1 nm, and AgMg (weightratio of 10:1) were co-deposited on the electron injection layer to forma cathode having a thickness of 10 nm, thereby completing themanufacture of an organic light-emitting device.

Examples 2 to 6 and Comparative Examples 1 to 3

Organic light-emitting devices were manufactured in substantially thesame manner as in Example 1, except that Compounds shown in Table 5 wererespectively used in forming an electron blocking layer.

Evaluation Example

The driving voltage, current efficiency, brightness, and lifespan of theorganic light-emitting devices manufactured according to Examples 1 to 6and Comparative Examples 1 to 3 were measured at a current density of 50mA/cm² by using Keithley SMU 236 and a luminance meter PR650, andresults thereof are shown in Table 5. The lifespan indicates an amountof time when luminance was 97% of initial luminance (100%).

TABLE 5 Electron Driving Luminance blocking voltage Efficiency lifespanBrightness layer (V) (cd/A) (T97, Hr) (1,000 nit) Example 1 Compound 14.3 6.6 145 1000 Example 2 Compound 2 4.1 6.4 155 1000 Example 3Compound 3 4.0 6.7 175 1000 Example 4 Compound 4 4.2 6.8 133 1000Example 5 Compound 5 3.9 6.4 188 1000 Example 6 Compound 6 4.0 6.3 1351000 Comparative Compound A 4.4 6.0 95 1000 Example 1 ComparativeCompound B 4.4 6.3 100 1000 Example 2 Comparative TCTA 4.1 6.2 10 1000Example 3

Referring to Table 1, it is confirmed that the luminance lifespans ofthe organic light-emitting devices of Examples 1 to 6 are veryexcellent, as compared with those of the organic light-emitting devicesof Comparative Examples 1 to 3. Although not limited to a specificmechanism or theory, Compounds A and B have BDEs similar to those ofCompounds 1 to 6, but hole injection from the electron blocking layer tothe emission layer may not be smoothly performed because hole mobilityis very low. Therefore, in spite of the high BDE of Compounds A and B,host compounds in the organic light-emitting devices of ComparativeExamples 1 and 2 are deteriorated due to high electron density in theemission layer, thereby reducing the lifespan thereof. In addition,because TCTA has significantly low BDE as compared with Compounds 1 to6, it is confirmed that the luminance lifespan of the organiclight-emitting device is very short.

The organic light-emitting device according to embodiments of thepresent disclosure may have a low driving voltage, high luminance, highefficiency, and a long lifespan.

It should be understood that embodiments described herein should beconsidered in a descriptive sense only and not for purposes oflimitation. Descriptions of features or aspects within each embodimentshould typically be considered as available for other similar featuresor aspects in other embodiments.

It will be understood that, although the terms “first,” “second,”“third,” etc., may be used herein to describe various elements,components, regions, layers and/or sections, these elements, components,regions, layers and/or sections should not be limited by these terms.These terms are used to distinguish one element, component, region,layer or section from another element, component, region, layer orsection. Thus, a first element, component, region, layer or sectiondescribed below could be termed a second element, component, region,layer or section, without departing from the spirit and scope of thepresent disclosure.

Spatially relative terms, such as “beneath,” “below,” “lower,” “under,”“above,” “upper,” and the like, may be used herein for ease ofexplanation to describe one element or feature's relationship to anotherelement(s) or feature(s) as illustrated in the figures. It will beunderstood that the spatially relative terms are intended to encompassdifferent orientations of the device in use or in operation, in additionto the orientation depicted in the figures. For example, if the devicein the figures is turned over, elements described as “below” or“beneath” or “under” other elements or features would then be oriented“above” the other elements or features. Thus, the example terms “below”and “under” can encompass both an orientation of above and below. Thedevice may be otherwise oriented (e.g., rotated 90 degrees or at otherorientations) and the spatially relative descriptors used herein shouldbe interpreted accordingly.

As used herein, the terms “substantially,” “about,” and similar termsare used as terms of approximation and not as terms of degree, and areintended to account for the inherent deviations in measured orcalculated values that would be recognized by those of ordinary skill inthe art. Further, the use of “may” when describing embodiments of thepresent disclosure refers to “one or more embodiments of the presentdisclosure.” As used herein, the terms “use,” “using,” and “used” may beconsidered synonymous with the terms “utilize,” “utilizing,” and“utilized,” respectively. Also, the term “exemplary” is intended torefer to an example or illustration.

Also, any numerical range recited herein is intended to include allsub-ranges of the same numerical precision subsumed within the recitedrange. For example, a range of “1.0 to 10.0” is intended to include allsubranges between (and including) the recited minimum value of 1.0 andthe recited maximum value of 10.0, that is, having a minimum value equalto or greater than 1.0 and a maximum value equal to or less than 10.0,such as, for example, 2.4 to 7.6. Any maximum numerical limitationrecited herein is intended to include all lower numerical limitationssubsumed therein, and any minimum numerical limitation recited in thisspecification is intended to include all higher numerical limitationssubsumed therein. Accordingly, Applicant reserves the right to amendthis specification, including the claims, to expressly recite anysub-range subsumed within the ranges expressly recited herein.

While one or more embodiments have been described with reference to thefigures, it will be understood by those of ordinary skill in the artthat various changes in form and details may be made therein withoutdeparting from the spirit and scope as defined by the following claims,and equivalents thereof.

What is claimed is:
 1. A condensed cyclic compound represented byFormula 1:(A₁₁)_(n11)-(L₁₁)_(a11)-(A₁₂)_(n12),   Formula 1 wherein, in Formula 1,L₁₁ is selected from a substituted or unsubstituted C₅-C₆₀ carbocyclicgroup and a substituted or unsubstituted C₁-C₆₀ heterocyclic group, a11is an integer of 0 to 5, A₁₁ and A₁₂ are each independently selectedfrom a group represented by Formula 1A and a group represented byFormula 1B, and n11 and n12 are each independently an integer from 1 to3:

wherein, in Formulae 1A and 1B, X₁₁ is selected from C(R₁₄)(R₁₅),Si(R₁₄)(R₁₅), O, and S, X₁₂ is selected from C(R₁₆)(R₁₇), Si(R₁₆)(R₁₇),O, and S, R₁₁ to R₁₇ are each independently selected from hydrogen,deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitrogroup, a substituted or unsubstituted C₁-C₆₀ alkyl group, a substitutedor unsubstituted C₂-C₆₀ alkenyl group, a substituted or unsubstitutedC₂-C₆₀ alkynyl group, a substituted or unsubstituted C₁-C₆₀ alkoxygroup, a substituted or unsubstituted C₃-C₁₀ cycloalkyl group, asubstituted or unsubstituted C₁-C₁₀ heterocycloalkyl group, asubstituted or unsubstituted C₃-C₁₀ cycloalkenyl group, a substituted orunsubstituted C₁-C₁₀ heterocycloalkenyl group, a substituted orunsubstituted C₆-C₆₀ aryl group, a substituted or unsubstituted C₆-C₆₀aryloxy group, a substituted or unsubstituted C₆-C₆₀ arylthio group, asubstituted or unsubstituted C₁-C₆₀ heteroaryl group, a substituted orunsubstituted C₁-C₆₀ heteroaryloxy group, a substituted or unsubstitutedC₁-C₆₀ heteroarylthio group, a substituted or unsubstituted monovalentnon-aromatic condensed polycyclic group, a substituted or unsubstitutedmonovalent non-aromatic condensed heteropolycyclic group,—Si(Q₁)(Q₂)(Q₃), —B(Q₁)(Q₂), —N(Q₁)(Q₂), —P(Q₁)(Q₂), —C(═O)(Q₁),—S(═O)(Q₁), —S(=O)₂(Q₁), —P(═O)(Q₁)(Q₂), and —P(═S)(Q₁)(Q₂), b11 isselected from 1 and 2, b12 and b13 are each independently an integerfrom 1 to 3, Q₁ to Q₃ are each independently selected from hydrogen,deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitrogroup, a C₁-C₆₀ alkyl group, a C₂-C₆₀ alkenyl group, a C₂-C₆₀ alkynylgroup, a C₁-C₆₀ alkoxy group, a C₃-C₁₀ cycloalkyl group, a C₁-C₁₀heterocycloalkyl group, a C₃-C₁₀ cycloalkenyl group, a C₁-C₁₀heterocycloalkenyl group, a C₆-C₆₀ aryl group, a C₆-C₆₀ aryloxy group, aC₆-C₆₀ arylthio group, a C₁-C₆₀ heteroaryl group, a C₁-C₆₀ heteroaryloxygroup, a C₁-C₆₀ heteroarylthio group, a monovalent non-aromaticcondensed polycyclic group, a monovalent non-aromatic condensedheteropolycyclic group, a biphenyl group, and a terphenyl group, and *indicates a binding site to a neighboring atom.
 2. The condensed cycliccompound of claim 1, wherein: L₁₁ is selected from groups represented byFormulae 4-1 to 4-35;

wherein, in Formulae 4-1 to 4-35, X₄₁ is C(R₄₃)(R₄₄), R₄₁ to R₄₄ areeach independently selected from hydrogen, deuterium, —F, —Cl, —Br, —I,a hydroxyl group, a cyano group, a nitro group, a C₁-C₂₀ alkyl group, aC₁-C₂₀ alkoxy group, a phenyl group, a biphenyl group, a terphenylgroup, a naphthyl group, a fluorenyl group, a spiro-bifluorenyl group, abenzofluorenyl group, a dibenzofluorenyl group, a phenanthrenyl group,an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, apyrenyl group, a chrysenyl group, and a perylenyl group, b41 is selectedfrom 1, 2, 3, and 4, b42 is selected from 1, 2, 3, 4, 5, and 6, b43 isselected from 1, 2, 3, 4, 5, 6, 7, and 8, b44 is selected from 1, 2, 3,4, and 5, b45 is selected from 1, 2, and 3, b46 is selected from 1 and2, and * and *′ each indicate a binding site to a neighboring atom. 3.The condensed cyclic compound of claim 2, wherein: L₁₁ is selected fromgroups represented by Formulae 4-1 to 4-12.
 4. The condensed cycliccompound of claim 1, wherein: a11 is selected from 0, 1, and
 2. 5. Thecondensed cyclic compound of claim 1, wherein: n11 and n12 are eachindependently selected from 1 and
 2. 6. The condensed cyclic compound ofclaim 1, wherein: the sum of n11 and n12 is selected from 2 and
 3. 7.The condensed cyclic compound of claim 1, wherein: X₁₁ is C(R₁₄)(R₁₅),and X₁₂ is C(R₁₆)(R₁₇).
 8. The condensed cyclic compound of claim 1,wherein: R₁₁ to R₁₇ are each independently selected from: hydrogen,deuterium, —F, —Cl, —Br, —I, a cyano group, a C₁-C₂₀ alkyl group, and aC₁-C₂₀ alkoxy group; a C₁-C₂₀ alkyl group and a C₁-C₂₀ alkoxy group,each substituted with at least one selected from deuterium, —F, —Cl,—Br, —I, a cyano group, a phenyl group, a biphenyl group, and aterphenyl group; a cyclopentyl group, a cyclohexyl group, a cycloheptylgroup, a cyclopentenyl group, a cyclohexenyl group, a phenyl group, abiphenyl group, a terphenyl group, a pentalenyl group, an indenyl group,a naphthyl group, an azulenyl group, an indacenyl group, an acenaphthylgroup, a fluorenyl group, a spiro-bifluorenyl group, a benzofluorenylgroup, a dibenzofluorenyl group, a phenalenyl group, a phenanthrenylgroup, an anthracenyl group, a fluoranthenyl group, a triphenylenylgroup, a pyrenyl group, a chrysenyl group, a perylenyl group, and apentacenyl group; and a cyclopentyl group, a cyclohexyl group, acycloheptyl group, a cyclopentenyl group, a cyclohexenyl group, a phenylgroup, a biphenyl group, a terphenyl group, a pentalenyl group, anindenyl group, a naphthyl group, an azulenyl group, an indacenyl group,an acenaphthyl group, a fluorenyl group, a spiro-bifluorenyl group, abenzofluorenyl group, a dibenzofluorenyl group, a phenalenyl group, aphenanthrenyl group, an anthracenyl group, a fluoranthenyl group, atriphenylenyl group, a pyrenyl group, a chrysenyl group, a perylenylgroup, and a pentacenyl group, each substituted with at least oneselected from deuterium, —F, —Cl, —Br, —I, a cyano group, a C₁-C₂₀ alkylgroup, a C₁-C₂₀ alkoxy group, a cyclopentyl group, a cyclohexyl group, acycloheptyl group, a cyclopentenyl group, a cyclohexenyl group, a phenylgroup, a biphenyl group, a terphenyl group, a pentalenyl group, anindenyl group, a naphthyl group, an azulenyl group, an indacenyl group,an acenaphthyl group, a fluorenyl group, a spiro-bifluorenyl group, abenzofluorenyl group, a dibenzofluorenyl group, a phenalenyl group, aphenanthrenyl group, an anthracenyl group, a fluoranthenyl group, atriphenylenyl group, a pyrenyl group, a chrysenyl group, a perylenylgroup, and a pentacenyl group.
 9. The condensed cyclic compound of claim1, wherein: R₁₁ to R₁₇ are each independently selected from: hydrogen,deuterium, —F, —Cl, —Br, —I, a cyano group, and a C₁-C₂₀ alkyl group; aC₁-C₂₀ alkyl group substituted with at least one selected fromdeuterium, —F, —Cl, —Br, —I, and a cyano group; and groups representedby Formulae 5-1 to 5-9:

wherein, in Formulae 5-1 to 5-9, R₅₁ and R₅₂ are each independentlyselected from hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, acyano group, a nitro group, a C₁-C₂₀ alkyl group, a C₁-C₂₀ alkoxy group,a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, afluorenyl group, a spiro-bifluorenyl group, a benzofluorenyl group, adibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, afluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenylgroup, and a perylenyl group, b51 is selected from 1, 2, 3, 4, and 5,b52 is selected from 1, 2, 3, 4, 5, 6, and 7, b53 is selected from 1, 2,3, 4, 5, 6, 7, 8, and 9, b54 is selected from 1, 2, 3, and 4, and *indicates a binding site to a neighboring atom.
 10. The condensed cycliccompound of claim 1, wherein: the condensed cyclic compound isrepresented by one selected from Formulae 1-1 and 1-2:

wherein, in Formulae 1-1 and 1-2, L₁₁ and a11 are each independently thesame as defined in connection with Formula 1, X_(11a) and X_(11b) areeach independently the same as defined in connection with s X₁₁ inFormula 1A, X_(12a) and X_(12b) are each independently the same asdefined in connection with X₁₂ in Formula 1A, R_(11a), R_(11b), R_(12a),R_(12b), R_(13a), and R_(13b) are each independently the same as definedin connection with R₁₁ in Formula 1A, b11a and b11b are eachindependently the same as defined in connection with b11 in Formula 1A,and b12a, b12b, b13a, and b13b are each independently the same asdefined in connection with b12 in Formula 1A.
 11. The condensed cycliccompound of claim 1, wherein: the condensed cyclic compound isrepresented by one selected from Formulae 1-11 and 1-12:

wherein, in Formulae 1-11 and 1-12, L₁₁ is selected from groupsrepresented by Formulae 4-1 to 4-12:

wherein, in Formulae 4-1 to 4-12, R₄₁ is selected from hydrogen,deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitrogroup, a C₁-C₂₀ alkyl group, a C₁-C₂₀ alkoxy group, a phenyl group, abiphenyl group, a terphenyl group, a naphthyl group, a fluorenyl group,a spiro-bifluorenyl group, a benzofluorenyl group, a dibenzofluorenylgroup, a phenanthrenyl group, an anthracenyl group, a fluoranthenylgroup, a triphenylenyl group, a pyrenyl group, a chrysenyl group, and aperylenyl group, b41 is selected from 1, 2, 3, and 4, b42 is selectedfrom 1, 2, 3, 4, 5, and 6, * and *′ each indicate a binding site to aneighboring atom, a11 is selected from 0, 1, and 2, R_(11a), R_(11b),R_(12a), R_(12b), R_(13a), R_(13b), R_(14a), R_(14b), R_(15a), R_(15b),R_(16a), R_(16b), R_(17a), and R_(17b) are each independently the sameas defined in connection with R₁₁ in Formula 1A, b11a and b11b are eachindependently the same as defined in connection with b11 in Formula 1A,and b12a, b12b, b13a, and b13b are each independently defined the sameas b12 in Formula 1A.
 12. The condensed cyclic compound of claim 1,wherein: the condensed cyclic compound is selected from Compounds 1 to6:


13. The condensed cyclic compound of claim 1, wherein: a bonddissociation energy of the condensed cyclic compound is greater thanabout 1.8 eV.
 14. An organic light-emitting device comprising: a firstelectrode; a second electrode; and an organic layer between the firstelectrode and the second electrode and comprising an emission layer,wherein the organic layer comprises the condensed cyclic compound ofclaim
 1. 15. The organic light-emitting device of claim 1, wherein: theemission layer comprises the condensed cyclic compound.
 16. The organiclight-emitting device of claim 1, wherein: the first electrode is ananode, the second electrode is a cathode, the organic layer furthercomprises a hole transport region between the first electrode and theemission layer and/or an electron transport region between the emissionlayer and the second electrode, the hole transport region comprises ahole injection layer, a hole transport layer, an emission auxiliarylayer, an electron blocking layer, or any combination thereof, and theelectron transport region comprises a hole blocking layer, an electrontransport layer, an electron injection layer, or any combinationthereof.
 17. The organic light-emitting device of claim 16, wherein: theelectron blocking layer comprises the condensed cyclic compound.
 18. Theorganic light-emitting device of claim 17, wherein: the emission layercomprises a host and satisfies Condition 1:BDE(C ⁻)>T ₁(H),   Condition 1 wherein, in Condition 1, BDE(C⁻) is abond dissociation energy of the condensed cyclic compound in an anionstate, and T₁(H) is a lowest excitation triplet energy level of thehost.
 19. The organic light-emitting device of claim 17, wherein: theemission layer comprises a host and satisfies Condition 2:|HOMO (H)−HOMO (C)|≤0.3 eV,   Condition 2 wherein, in Condition 2, HOMO(H) is a highest occupied molecular orbital energy level of the host,and HOMO (C) is a highest occupied molecular orbital energy level of thecondensed cyclic compound.
 20. A display apparatus comprising: athin-film transistor comprising a source electrode, a drain electrode,and an active layer; and the organic light-emitting device of claim 14,wherein the first electrode of the organic light-emitting device iselectrically coupled to one selected from the source electrode and thedrain electrode of the thin-film transistor.